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Chemical Structure| 76205-19-1 Chemical Structure| 76205-19-1

Structure of 76205-19-1

Chemical Structure| 76205-19-1

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CAS No.: 76205-19-1

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Product Details of [ 76205-19-1 ]

CAS No. :76205-19-1
Formula : C9H7ClN2O
M.W : 194.62
SMILES Code : OC1=NN(C=C1)C1=CC=C(Cl)C=C1
MDL No. :MFCD08459260
InChI Key :DRENHOMDLNJDOG-UHFFFAOYSA-N
Pubchem ID :11356026

Safety of [ 76205-19-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 76205-19-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 11
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 50.6
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

38.05 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.09
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.5
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.23
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.1
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.11

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.18
Solubility 0.128 mg/ml ; 0.000658 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.94
Solubility 0.221 mg/ml ; 0.00114 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.97
Solubility 0.208 mg/ml ; 0.00107 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.71 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.64

Application In Synthesis of [ 76205-19-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 76205-19-1 ]

[ 76205-19-1 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 76205-19-1 ]
  • [ 162225-07-2 ]
  • [ 235441-18-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium tert-butylate; dimethyl sulfoxide; In cyclohexane; ethyl acetate; tert-butyl alcohol; 1a. Methyl [2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]glyoxylate At 60° C., 4.7 g (42 mmol) of potassium tert-butoxide were added a little at a time to a solution of 7.4 g (38.1 mmol) of <strong>[76205-19-1]1-(4-chlorophenyl)-3-hydroxypyrazole</strong> in 15 ml of tert-butanol. The mixture was stirred at this temperature for 1 hour and the solvent was then removed under reduced pressure. The residue was dissolved in 25 ml of abs. dimethyl sulfoxide, and a solution of 8.0 g (38.1 mmol) of methyl (2-chloropyridin-3-yl)glyoxylate in 10 ml of abs. dimethyl sulfoxide was then added at such a rate that the temperature did not exceed 30° C. After 30 minutes at room temperature, 50 ml of 0.5 N HCl were added and the reaction mixture was extracted repeatedly with ethyl acetate. The combined organic phases were washed with water and dried over sodium sulfate. The solvent was subsequently removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using cyclohexane/ethyl acetate (10:1) as eluant. 5.5 g (40percent) of the title compound were obtained as a clear oil.
  • 2
  • [ 76205-19-1 ]
  • [ 206198-90-5 ]
  • (ortho-[1-{4-chlorophenyl}-pyrazol-3-yl-oxymethyl]-phenyl)(5,6-dihydro-[1,4,2]dioxazin-3-yl)methanone O-methyl oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; water; Example 3 Synthesis of (ortho-[1-{4-chlorophenyl}-pyrazol-3-yl-oxymethyl]- phenyl)(5,6-dihydro-[1,4,2]dioxazin-3-yl)methanone O-methyl oxime A solution of 0.97 g of <strong>[76205-19-1]1-(para-chlorophenyl)-3-hydroxypyrazole</strong> in 20 ml of anhydrous dimethylformamide (DMF) was admixed with 0.13 g of sodium hydride and then stirred at 20-25 ° C. for approximately one hour. 1.34 g of the oxime from Example 2 were then added and the mixture was stirred at 60° C. for approximately three hours and then at 20-25° C. for approximately 14 hours. 300 ml of water were added and the mixture was then extracted with methyl tert-butyl ether (MTBE). The combined organic phases were washed with water and dried, and the solvent was then removed. The residue was chromatographed over silica gel (cyclohexane/ethyl acetate mixture [1:1]), giving 1.15 g of the title compound as a light-beige amorphous powder of m.p. 56-59° C. IR [cm-1]: 1546, 1502, 1480, 1464, 1358, 1093, 1054, 998, 935, 906.
  • 3
  • [ 6119-12-6 ]
  • [ 71-48-7 ]
  • [ 76205-19-1 ]
YieldReaction ConditionsOperation in experiment
In potassium hydroxide; 13. Preparation of 1-(4-chlorophenyl)-3-hydroxypyrazole using pure oxygen with Co(II) catalysis 900 g of a 6.9percent strength solution of 1-(4-chlorophenyl)-pyrazolidin-3-one in 5percent strength potassium hydroxide solution were admixed with 600 mg of cobalt(II) acetate and oxygen was passed into the solution at room temperature via a capillary in such a manner that it was just completely absorbed. After approximately 30 min, the reaction was complete according to HPLC monitoring, the temperature having increased to 40° C. 908 g of a solution were obtained which had a 1-(4-chlorophenyl)-3-hydroxypyrazole content of 6.7percent.
  • 4
  • [ 6119-12-6 ]
  • [ 76205-19-1 ]
YieldReaction ConditionsOperation in experiment
99.7% With iron(III) chloride; acetic acid; at 50℃; for 4h; First, 60 g of acetic acid was added to the apparatus,19.66 g (0.1 mol) of 1- (4-chlorophenyl) pyrazolidin-3-one was added with stirring,0.0162 g (0.0001 mol) of ferric chloride, and the temperature was raised to 50 C,4h after removing most of the solvent, add water, stirring, a large number of product precipitation,With sodium hydroxide solution to adjust the pH value to 7, continue stirring 0.5h,The yield was 99.7% and the content was 99.6% (LC), which was obtained by filtration to obtain 19.4 g of 1- (4-chlorophenyl) -3-pyrazolol.
91.2% With dipotassium peroxodisulfate; sulfuric acid; In acetonitrile; for 6h;Reflux; With a mechanical stir,Reflux condenser and a thermometer in a 250 ml four-necked reaction flask were charged with 19.6 g (0.1 mol)1- (4-chlorophenyl) pyrazolidin-3-one and 100 ml of acetonitrile,After stirring and dissolving,2 g (0.02 mol) of concentrated sulfuric acid and 32.4 g were added(0.12 mil) potassium persulfate,In 30-80 C (the optimum temperature of 75-80 C) heating reflux 6h,Most of the solvent B is distilled offNitrile,Cooled by adding 50 ml of water,With hydrochloric acid to adjust the pH to 1,Filtered and dried to obtain 17.7 g of product,Yield 91.2%.
84.2% With hydrogenchloride; sodium nitrite; In water; for 3h;Inert atmosphere; Cooling with ice; Under a nitrogen atmosphere, 0.80 g of 1-(4- chlorophenyl)pyrazolidin-3-one, 1.03 g of concentrated hydrochloric acid, and 3.0 g of water were mixed and ice-cooled. To this mixture, an aqueous solution prepared by dissolving 565.8 mg of sodium nitrite in 1.14 g of water was added dropwise. The obtained mixture was stirred with ice-cooling for 3 hours, water was added, and then the solid was collected by filtration. The obtained solid was washed with water and then hexane, followed by drying to give 0.80 g of 4-chlorophenyl-1H-pyrazol-3-ol (content: 83.3 wt %). Yield: 84.1%.
With potassium hydroxide; potassium hexacyanoferrate(III); In water; 6. Preparation of 1-(4-chlorophenyl)-3-hydroxypyrazole using air with potassium hexacyanoferrate(III) catalysis 98.3 g of 1-(4-chlorophenyl)pyrazolidin-3-one were dissolved in a mixture of 641.3 g of water and 33.75 g of potassium hydroxide and 0.98 g of potassium hexacyanoferrate(III) were added. The mixture was heated to 80 C., passing in a vigorous air stream through a capillary, and was then further oxidized at this temperature. After cooling, the mixture was acidified to pH 2 with concentrated sulfuric acid. The solid separating off was filtered off with suction, washed with water and diisopropyl ether and dried. 76 g of a light-brown solid remained.
With acetic acid; In water; 8. Preparation of 1-(4-chlorophenyl)-3-hydroxypyrazole using pure oxygen without catalysis under pressure The solution of 9.75 g of 1-(4-chlorophenyl)pyrazolidin-3-one in 150 g of water was charged into a 300 ml autoclave. Oxygen at 15 bar was then forced in; the mixture was heated to 50 C. and allowed to stand for six hours at this temperature. The mixture was cooled and adjusted to a pH of 5 by adding acetic acid. The solid which precipitated out was filtered off with suction, digested in water for 30 minutes at 60 C., and again filtered off with suction and dried. 9.4 g of the product remained as colorless powder having a content of 95.4%.
In potassium hydroxide; 12. Preparation of 1-(4-chlorophenyl)-3-hydroxypyrazole using pure oxygen without catalysis 850 g of a 7.4% strength solution of 1-(4-chlorophenyl)-pyrazolidin-3-one in 5% strength potassium hydroxide solution were heated to 60 C. oxygen was introduced into the solution via a capillary in such a manner that it was just completely absorbed. After approximately 90 min, the reaction was complete according to monitoring by HPLC. 855 g of a solution were obtained which had a 1-(4-chlorophenyl)-3-hydroxypyrazole content of 7.3%.

  • 5
  • [ 205178-82-1 ]
  • [ 922-67-8 ]
  • [ 76205-19-1 ]
YieldReaction ConditionsOperation in experiment
In potassium tert-butylate; water; tert-butyl alcohol; 1.b 1-(4-Chlorophenyl)-3-hydroxypyrazole A solution of 57.5 g of 4-chlorophenylhydrazine hydrosulfate in 1,000 ml of tert-butanol was first treated in portions with 100.8 g of potassium tert-butoxide and then (after stirring for 10 min) in the course of 45 min at 45° C.-50° C. with a solution of 27.7 g of methyl propiolate in 90 ml of tertbutanol. After 1 h at boiling point, the mixture was allowed to cool and the solvent was removed under reduced pressure. The residue thus obtained was dissolved in 1,200 ml of water. The aqueous phase was first washed with methylene chloride and then acidified, the product being deposited as a solid. 47.6 g of the title compound were obtained, m.p.: 185°-187° C.
  • 6
  • [ 76205-19-1 ]
  • [ 1284183-66-9 ]
  • 7
  • [ 76205-19-1 ]
  • [ 1284183-67-0 ]
  • 8
  • [ 76205-19-1 ]
  • [ 1284183-69-2 ]
  • 9
  • [ 76205-19-1 ]
  • [ 1284183-62-5 ]
  • [ 1284183-64-7 ]
  • 11
  • [ 76205-19-1 ]
  • [ 1334322-60-9 ]
  • [ 175013-18-0 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; Example 12; /S/-{2-[/S/'-(4-chloro-phenyl)-pyrazol-3'-oxymethyl]-phenyl}-A/-methoxy-carbamic acid methyl ester; A/-Carbomethoxy-A/-methoxy-(2-chloromethyl)-aniline (0.20 g, 0.87 mmol), 1 -(4-chloro- phenyl)-3-hydroxypyrrazole (0.17 g, 0.87 mmol) and K2CO3 were suspended in DMF (10 ml). The reaction mixture was stirred at 50 °C overnight. Thin layer chromatography control showed complete consumption of both starting materials. The suspension was diluted with tert-butyl methyl ether (100 ml), extracted four times with water and dried over MgSC . The crude product could be optionally purified by column chromatography on S1O2 to give the desired product (0.25 g, 0.64 mmol, 74percent yield). Alternatively, the product could be purified by recrystallization from ethanol/hbO (3:1 (v/v)).
74% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; Example 12N-{2-[N'-(4-chloro-phenyl)-pyrazol-3'-oxymethyl]-phenyl}-N-methoxy-carbamic acid methyl esterN-Carbomethoxy-N-methoxy-(2-chloromethyl)-aniline (0.20 g, 0.87 mmol), 1-(4-chloro-phenyl)-3-hydroxypyrrazole (0.17 g, 0.87 mmol) and K2CO3 were suspended in DMF (10 ml). The reaction mixture was stirred at 50° C. overnight. Thin layer chromatography control showed complete consumption of both starting materials. The suspension was diluted with tert-butyl methyl ether (100 ml), extracted four times with water and dried over MgSO4. The crude product could be optionally purified by column chromatography on SiO2 to give the desired product (0.25 g, 0.64 mmol, 74percent yield). Alternatively, the product could be purified by recrystallization from ethanol/H2O (3:1 (v/v)).
  • 12
  • [ 76205-19-1 ]
  • [ 76205-20-4 ]
YieldReaction ConditionsOperation in experiment
85% With thionyl chloride; N,N-dimethyl-formamide;Reflux; General procedure: A mixture of SOCl2 (5 mL), Ia?Id (1.0 mmol), and a catalytic amount of DMF (0.1 mmol) wereheated under reflux for about 4 h (monitored by TLC), then excess SOCl2 was evaporated and H2O(200 mL) was added with good stirring. The precipitate that formed was filtered off, washed with H2O, andthen purified by a silica-gel column chromatography (petroleum ether/EtOAc = 5:1) to afford IIa?IId.
  • 13
  • [ 76205-19-1 ]
  • [ 1257339-28-8 ]
  • [ 1257338-98-9 ]
  • 15
  • [ 3240-94-6 ]
  • [ 76205-19-1 ]
  • [ 1392758-90-5 ]
  • 16
  • [ 1073-69-4 ]
  • [ 623-47-2 ]
  • [ 76205-19-1 ]
  • 17
  • [ 76205-19-1 ]
  • [ 78-95-5 ]
  • [ 1445342-06-2 ]
YieldReaction ConditionsOperation in experiment
5.50 g (28.3 mmol) 1 -(4-chlorophenyl)pyrazol-3-ol, 3.91 g (28.3 mmol) potassium carbonate and 50 mg sodium iodide in 30 ml DMF have been stirred for 5 min at ambient temperature. Then 2.62 g (28.3 mmol) chloroacetone have been added dropwise while stirring which was continued at 60°C for 5 h. The mixture was poured into excess 10 percent aqueous lithium chloride solution and extracted with ethyl acetate three times. The combined extracts have been washed with 10 percent lithium chloride solution twice and dried with sodium sulfate. After removal of the solvent in vacuo the crude product has been purified by chromatography on silica. Yield 6.5 g. The product was used for the next step.
Ex. 4a 1-[1-(4-Chlorophenyl)pyrazol-3-yl]oxypropan-2-one (11) 5.50 g (28.3 mmol) 1-(4-chlorophenyl)pyrazol-3-ol, 3.91 g (28.3 mmol) potassium carbonate and 50 mg sodium iodide in 30 ml DMF have been stirred for 5 min at ambient temperature. Then 2.62 g (28.3 mmol) chloroacetone have been added dropwise while stirring which was continued at 60° C. for 5 h. The mixture was poured into excess 10percent aqueous lithium chloride solution and extracted with ethyl acetate three times. The combined extracts have been washed with 10percent lithium chloride solution twice and dried with sodium sulfate. After removal of the solvent in vacuo the crude product has been purified by chromatography on silica. Yield 6.5 g. The product was used for the next step.
  • 18
  • [ 76205-19-1 ]
  • cis-[3-methyloxiran-2-yl]methanol [ No CAS ]
  • (±)-1-(4-chlorophenyl)-3-[[(2R,3S)-3-methyloxiran-2-yl]methoxy]pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.5 g To 28.3 g (107.9 mmol) triphenylphosphine and 15. Og (127.7 mmol) cis-3- methyloxiran-2-yl]methanol (15) from the preceding experiment in 400 ml THF have been added with stirring at -75°C 22.9 g (1 13.0 mmol) azodicarbonic acid diisopropyl ester. The mixture has been stirred at this temperature for 5 min. Then 20.0 g (102.8 mmol) 1 -(4-chlorophenyl)-3-hydroxypyrazole have been added with stirring at - 70°C. The mixture was allowed to warm up to ambient temperature and stirred for about 1 d. After removal of the solvents in vacuo the crude product was stirred with 200 ml of diisopropylether from which 42 g of a solid substance have been collected and further purified by chromatography on 330 g silica with MTBE/heptane. Yield 22.5 g (82percent)
22.5 g Ex. 5b Racemic 1-(4-chlorophenyl)-3-[[(2R,3S)-3-methyloxiran-2-yl]methoxy]pyrazole (16) To 28.3 g (107.9 mmol) triphenylphosphine and 15.0 g (127.7 mmol) cis-3-methyloxiran-2-yl]methanol (15) from the preceding experiment in 400 ml THF have been added with stirring at -75° C. 22.9 g (113.0 mmol) azodicarbonic acid diisopropyl ester. The mixture has been stirred at this temperature for 5 min. Then 20.0 g (102.8 mmol) <strong>[76205-19-1]1-(4-chlorophenyl)-3-hydroxypyrazole</strong> have been added with stirring at -70° C. The mixture was allowed to warm up to ambient temperature and stirred for about 1d. After removal of the solvents in vacuo the crude product was stirred with 200 ml of diisopropylether from which 42 g of a solid substance have been collected and further purified by chromatography on 330 g silica with MTBE/heptane. Yield 22.5 g (82percent).
  • 19
  • [ 76205-19-1 ]
  • [ 850354-34-6 ]
  • [ 1445341-96-7 ]
YieldReaction ConditionsOperation in experiment
75% To 8.09 g (30.8 mmol) triphenylphosphine in 200 ml THF have been added with stirring at -75°C 6.23 g (30.8 mmol) azodicarbonic acid diisopropyl ester. The mixture has been stirred at this temperature for 5 min. Then 10.39 g (28.8 mmol) (Z)-3-tributyl-stannanyl-but-2-en-1-ol have been added dropwise and stirred for 5 min at -75°C. After addition of 4.00 g (20.6 mmol) 1 -(4-chlorophenyl)-3-hydroxypyrazole at -75°C a red suspension was formed. The mixture was allowed to warm up to ambient temperature and stirred for 3 d. After removal of the solvents in vacuo 29 g oil have been collected and purified by chromatography on 120 g silica with MTBE/heptane. Yield 8.3 g (75percent) oil. delta = 0.85 (m); 0.95 (m); 1.30 (m); 1 .50 m); 2.00 (s); 4.65 (d); 5.90 (d); 6.43 (t); 7.35 (d); 7.52 (d); 7.68 (d).
75% Ex. 1b 1-(4-Chloro-phenyl)-3-((Z)-3-tributylstannanyl-but-2-enyloxy)-1H-pyrazole (5) To 8.09 g (30.8 mmol) triphenylphosphine in 200 ml THF have been added with stirring at -75° C. 6.23 g (30.8 mmol) azodicarbonic acid diisopropyl ester. The mixture has been stirred at this temperature for 5 min. Then 10.39 g (28.8 mmol) (Z)-3-tributylstannanyl-but-2-en-1-ol have been added dropwise and stirred for 5 min at -75° C. After addition of 4.00 g (20.6 mmol) <strong>[76205-19-1]1-(4-chlorophenyl)-3-hydroxypyrazole</strong> at -75° C. a red suspension was formed. The mixture was allowed to warm up to ambient temperature and stirred for 3 d. After removal of the solvents in vacuo 29 g oil have been collected and purified by chromatography on 120 g silica with MTBE/heptane. Yield 8.3 g (75percent) oil. delta=0.85 (m); 0.95 (m); 1.30 (m); 1.50 m); 2.00 (s); 4.65 (d); 5.90 (d); 6.43 (t); 7.35 (d); 7.52 (d); 7.68 (d).
  • 20
  • [ 76205-19-1 ]
  • C17H18ClN3O4 [ No CAS ]
  • 21
  • [ 76205-19-1 ]
  • [ 1445333-46-9 ]
  • 22
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 23
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.61 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 3) 1.21 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixture after standing to cool was added water, and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 1) 0.61 g. _,;Present tetrazolinone Compound 1 1H-NMR (CDCl3) delta(ppm): 7.64 (1H, d, J=2.7 Hz), 7.62-7.60 (1H, m), 7.53-7.49 (2H, m), 7.45 (1H, t, J=8.0 Hz), 7.39-7.35 (3H, m), 5.80 (1H, d, J=2.7 Hz), 5.54 (2H, s), 3.61 (3H, s).
1.61 g With potassium carbonate; In acetonitrile; for 4h;Reflux; Preparation Example 1 A mixture of 1-(2-bromomethyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 3) 1.21 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixture after standing to cool was added water, and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 1) 0.61 g. Present Tetrazolinone Compound 1 1H-NMR (CDCl3) delta (ppm): 7.64 (1H, d, J=2.7 Hz), 7.62-7.60 (1H, m), 7.53-7.49 (2H, m), 7.45 (1H, t, J=8.0 Hz), 7.39-7.35 (3H, m), 5.80 (1H, d, J=2.7 Hz), 5.54 (2H, s), 3.61 (3H, s).
0.61 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 3) 1.21 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixture after standing to cool was added water, and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl)-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 1) 0.61 g.
0.61 g With potassium carbonate; In acetonitrile; for 4h;Reflux; Reference Synthesis Example 3 according 1- (2-bromomethyl-3-chlorophenyl) -4-methyl-1,4-dihydro-tetrazol-5-one 1.21 g, 1- (4- chlorophenyl) -1H pyrazol-3-ol 0.78 g, heated to reflux and potassium carbonate 0.66 g and acetonitrile 30 mL was stirred for 4 hours. By adding water to the reaction mixture bangraeng, followed by extracting with ethyl acetate. To the organic layer was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By applying the resulting residue to silica gel column chromatography to give 1- (2 - [1- (4-chlorophenyl) -1H- pyrazol-3-yl] oxy} methyl-3-chlorophenyl) -4 methyl-1,4-dihydro-tetrazol-5-one (hereinafter referred to as the present compound tetra BBIT 1) to obtain 0.61 g.
0.61 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 3) 1.21 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixture after standing to cool was added water, and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 1) 0.61 g.
0.61 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 3) 1.21 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixture after standing to cool was added water, and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 1) 0.61 g. (0193) Present Tetrazolinone Compound 1 (0194) 1H-NMR (CDCl3) delta(ppm): 7.64 (1H, d, J=2.7 Hz), 7.62-7.60 (1H, m), 7.53-7.49 (2H, m), 7.45 (1H, t, J=8.0 Hz), 7.39-7.35 (3H, m), 5.80 (1H, d, J=2.7 Hz), 5.54 (2H, s), 3.61 (3H, s).

  • 24
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.6 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 6) 18.5 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 10.4 g, potassium carbonate 8.8 g and acetonitrile 400 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 2) 24.6 g.
24.6 g With potassium carbonate; In acetonitrile; for 4h;Reflux; Preparation Example 2 A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 6) 18.5 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 10.4 g, potassium carbonate 8.8 g and acetonitrile 400 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 2) 24.6 g.
24.6 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 6) 18.5 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 10.4 g, potassium carbonate 8.8 g and acetonitrile 400 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chiorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-bromophenyl)-4-methy1-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 2) 24.6 g.
24.6 g With potassium carbonate; In acetonitrile; for 4h;Reflux; Note described in Synthesis Example 6 1- (2-bromomethyl-3-bromo-phenyl) -4-methyl-1,4-dihydro-tetrazol-5-one 18.5 g, 1- (4- chlorophenyl) - 1H- pyrazol-3-ol 10.4 g, was stirred for 4 hours heating under reflux a mixture of potassium carbonate and 8.8 g of acetonitrile and 400 mL. By adding water to the reaction mixture bangraeng, followed by extracting with ethyl acetate.To the organic layer was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By applying the resulting residue to silica gel column chromatography to give 1- (2 - [1- (4-chlorophenyl) -1H- pyrazol-3-yl] oxy} methyl-3-bromophenyl) -4 -methyl-1,4-dihydro-tetrazol-5-one (hereinafter referred to as the tetra BBIT compound 2) was obtained 24.6 g.
24.6 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 6) 18.5 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 10.4 g, potassium carbonate 8.8 g and acetonitrile 400 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 2) 24.6 g.
24.6 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 6) 18.5 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 10.4 g, potassium carbonate 8.8 g and acetonitrile 400 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one thereinafter referred to as Present tetrazolinone compound 2) 24.6 g. (0196) Present Tetrazolinone Compound 2 (0197) 1H-NMR (CDCl3) delta(ppm): 7.81-7.79 (1H, m), 7.65 (1H, d, J=2.4 Hz), 7.54-7.50 (2H, m), 7.42-7.35 (4H, m), 5.81 (1H, d, J=2.4 Hz), 5.53 (2H, s), 3.60 (3H, s).

  • 25
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-iodophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-iodophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 26
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-methoxyphenyl)-4-methyl-1,4-dihydro-5H-tetrazole-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.97 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Exmaple 9) 1.20 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g, and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 5) 0.97 g. Present tetrazolinone Compound 5 1H-NMR (CDCl3) delta(ppm): 7.63 (1H, d, J=2.7 Hz), 7.53-7.49 (2H, m), 7.46 (1H, dd, J=8.5, 8.0 Hz), 7.38-7.34 (2H, m), 7.08 (1H, d, J=8.5 Hz), 7.04 (1H, d, J=8.0 Hz), 5.80 (1H, d, J=2.7 Hz), 5.43 (2H, s), 3.92 (3H, s), 3.57 (3H, s).
0.97 g With potassium carbonate; In acetonitrile; for 4h;Reflux; Preparation Example 5 A mixture of 1-(2-bromomethyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 9) 1.20 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g, and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 5) 0.97 g. Present Tetrazolinone Compound 5 1H-NMR (CDCl3) delta (ppm): 7.63 (1H, d, J=2.7 Hz), 7.53-7.49 (2H, m), 7.46 (1H, dd, J=8.5, 8.0 Hz), 7.38-7.34 (2H, m), 7.08 (1H, d, J=8.5 Hz), 7.04 (1H, d, J=8.0 Hz), 5.80 (1H, d, J=2.7 Hz), 5.43 (2H, s), 3.92 (3H, s), 3.57 (3H, s)
0.97 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Exmaple 9) 1.20 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g, and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 5) 0.97 g.
0.97 g With potassium carbonate; In acetonitrile; for 4h;Reflux; Note described in Synthesis Example 9 1- (2-bromomethyl-3-methoxy-phenyl) -4-methyl-1,4-dihydro-tetrazol-5-one 1.20 g, 1- (4- chlorophenyl) - 1H- pyrazol-3-ol 0.78 g, was stirred for 4 hours heating under reflux a mixture of potassium carbonate and 0.66 g of acetonitrile and 30 mL.By adding water to the reaction mixture bangraeng, followed by extracting with ethyl acetate.To the organic layer was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.By applying the resulting residue to silica gel column chromatography to give 1- (2 - [1- (4-chlorophenyl) -1H- pyrazol-3-yl] oxy} methyl-3-methoxyphenyl) -4 -methyl-1,4-dihydro-tetrazol-5-one (hereinafter referred to as the tetra BBIT compound 5) was obtained 0.97 g.
0.97 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 9) 1.20 g, <strong>[76205-19-1]1-(4-chlorophenyl)-1H-pyrazole-3-ol</strong> 0.78 g, potassium carbonate 0.66 g, and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 5) 0.97 g.
0.97 g With potassium carbonate; In acetonitrile; for 4h;Reflux; A mixture of 1-(2-bromomethyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation Example 9) 1.20 g, i-(4-chlorophenyl)-1H-pyrazole-3-ol 0.78 g, potassium carbonate 0.66 g, and acetonitrile 30 mL was stirred with heating under reflux for four hours. To the reaction mixtures after standing to cool was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-{([1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter referred to as Present tetrazolinone compound 5) 0.97 g. (0205) Present Tetrazolinone Compound 5 (0206) 1H-NMR (CDCl3) delta(ppm): 7.63 (1H, d, J=2.7 Hz), 7.53-7.49 (2H, m), 7.46 (1H, dd, J=8.5, 8.0 Hz), 7.38-7.34 (2H, m), 7.08 (1H, d, J=8.5 Hz), 7.04 (1H, d, J=8.0 Hz), 5.80 (1H, d, J=2.7 Hz), 5.43 (2H, s), 3.92 (3H, s), 3.57 (3H, s).

  • 27
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-(trifluoromethyl)phenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-(trifluoromethyl)phenyl)-4-methyl-1,4-dihydrotetrazol-5-thione [ No CAS ]
  • 28
  • [ 76205-19-1 ]
  • 1-(2-bromomethyl-3-nitrophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-nitrophenyl)-4-methyl-1,4-dihydrotetrazol-5-thione [ No CAS ]
  • 29
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-(difluoromethyl)phenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-(difluoromethyl)phenyl)-4-methyl-1,4-dihydrotetrazol-5-thione [ No CAS ]
  • 30
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-ethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-ethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 31
  • [ 76205-19-1 ]
  • 1-(2-(bromomethyl)-3-(methylthio)phenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
  • 1-(2-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}-3-(methylthio)phenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
 

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