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Chemical Structure| 98-60-2 Chemical Structure| 98-60-2
Chemical Structure| 98-60-2

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CAS No.: 98-60-2

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Product Details of [ 98-60-2 ]

CAS No. :98-60-2
Formula : C6H4Cl2O2S
M.W : 211.07
SMILES Code : O=S(C1=CC=C(Cl)C=C1)(Cl)=O
MDL No. :MFCD00007439
InChI Key :ZLYBFBAHAQEEQQ-UHFFFAOYSA-N
Pubchem ID :7398

Safety of [ 98-60-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:8
UN#:3261
Packing Group:Ⅱ

Calculated chemistry of [ 98-60-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 44.54
TPSA ?

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

42.52 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.81
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

1.84
Log Po/w (WLOGP)?

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

3.35
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.

2.11
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

1.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.22

Water Solubility

Log S (ESOL):?

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

-2.65
Solubility 0.478 mg/ml ; 0.00226 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.

-2.35
Solubility 0.935 mg/ml ; 0.00443 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

-3.56
Solubility 0.058 mg/ml ; 0.000275 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.

-6.28 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

 0.0
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)

 1.76

Application In Synthesis [ 98-60-2 ]

* 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 [ 98-60-2 ]

[ 98-60-2 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 98-60-2 ]
  • [ 97-08-5 ]
YieldReaction ConditionsOperation in experiment
71% With sulfuric acid; nitric acid; at 30 - 60℃; 1L three bottles were added 500mL concentrated H2SO4, p-chlorobenzenesulfonyl chloride 190g (0.9mol, 1eq) and heated to 30 C, dropping fuming nitric acid 56. 7g (0. 9mo 1,1 eq) to keep the temperature below 60 C, After the addition the internal temperature was stirred overnight at 55 C, TLC (PE / EA = 10/1). The reaction was cooled, poured into ice water, extracted with DCM, dried, filtered and concentrated to give 3-nitro-4-chlorobenzenesulfonyl chloride, white crystals 163g, yield 71%
  • 2
  • [ 98-60-2 ]
  • [ 14752-66-0 ]
YieldReaction ConditionsOperation in experiment
96% With Sodium hydrogenocarbonate; anhydrous sodium sulphite; In water monomer; at 80℃; for 4h; General procedure: At room temperature, the different substituents of benzenesulfonyl chloride (11mmol), sodium sulfite (22mmol),Sodium bicarbonate (22mmol) was dissolved in 50ml water, 80, 4h, TLC detection.After the reaction is complete, the reaction solution is evaporated to dryness, 30ml of methanol is added, and the reaction is heated at 78C for 1 hour.Filter off the insoluble matter while it is hot, evaporate the reaction solution, repeat the above steps to obtain sodium benzenesulfinate 3c-3f with different substituents.
94% With anhydrous sodium carbonate; anhydrous sodium sulphite; In water monomer; at 50℃; for 2h; General procedure: A solution of sodium sulfite (17.93g, 142.26 mmol) in H2O (100 ml) was stirred at room temperature for10 min. Sodium carbonate (23.90 g, 284.52 mmol)was added to the stirred solution.The resulting solution was stirred at 50 C for 10 minutes.cyclopropanesulfonyl chloride (20 g, 142.26 mmol) was added dropwise to thesolution and was stirred at 50 C for 2 hours. Thereaction mixture was evaporated to dryness and redissolved in EtOH (200 ml). The suspension was allowed to stir at roomtemperature for 20 min. The suspension was filtered and the filtrate evaporatedto afford a white solid, this was stirred with MeCN (50 ml) and thenfiltered to afford sodium cyclopropanesulfinicacid (13.70 g, 75 %) as a white solid. 1H NMR (400.132 MHz, DMSO d6)δ 1.38-1.31 (m, 1H), 0.27-0.24 (m,2H) and 0.08-0.03 (m, 2H).
With anhydrous sodium carbonate; sodium hydrogen sulphite; In water monomer; at 50℃; for 6h; Example 2: Preparation of 4,4'-dichlorophenyldisulfde271.3 g of an aqueous 25% sodium carbonate solution was added to 181.0 g of an aqueous 23% sodium bisulfite solution and the mixture was heated to 50 "C . 85.3 g of 99% /r?rα-chlorobenzenesulfonylchloride (containing 0.1% bis(4-chlorophenyl)sulfone) was added dropwise thereto over 2 hours and the resulting solution was stirred at 50 C for 4 hours. After cooling the reaction solution to 20 C, 44.4 g of 99% dichloromethane was added and bis(4-chlorophenyl)sulfone was then extracted, separated and removed.47.1 g of 50% sulfuric acid was added dropwise at 3 O0C for 1 hour to an aqueous 4-chlorobenzenesulfinate solution, from which bis(4-chlorophenyl)sulfone was removed, and 4.5 g of 57% iodic acid was then added dropwise thereto at that temperature in one portion. The reaction solution was elevated to 600C, then 95 C over 2 hours while introducing 51.2 g of sulfur dioxide gas for 5 hours and reacted at that temperature for 6 hours. After cooling to 200C, the reaction solution was extracted with 34.3 g of 99% dichloromethane to separate 4,4'-dichlorphenyldisulfide. 1.1 g of 50% sodium hydroxide and 1.3 g of 35% hydrogen peroxide (aqueous) were added to a solution of 4,4'-dichlorophenyldisulfide in dichloromethane which was then stirred at <n="16"/>room temperature for 1 hour, followed by separation of a dichloromethane layer. The separated dichloromethane layer was washed with 21.6 g of water and dichloromethane was removed by distillation under reduced pressure to afford 44.8 g (yield: 78%) of 4,4'-dichlorophenyldisulfide with 99.9% purity. A content of isomers in the thus- obtained product was 0.067%.21.4 g of 35% hydrogen peroxide (aqueous) was added dropwise to the aqueous solution separated from the solution of 4,4'-dichlorophenyldisulfide in dichloromethane and the resulting mixture was then stirred for 2 hours and separated by extraction with 45 g of 99% dichloromethane. Then, 4.3 g of 23% sodium bisulfite and 2.3 g of 50% sodium hydroxide were added dropwise to a solution of iodine separated in dichloromethane, followed by separation to recover 9.0 g (recovery rate: 95%) of an aqueous 31.7% sodium iodide solution. From analysis results of a final compound, it could be confirmed that the title compound was obtained as desired.
4.3 g With anhydrous sodium sulphite; In water monomer; at 80 - 90℃; for 1h; To chlorosulfonic acid (10 g, 86 mmol), chlorobenzene(3.23 g,28 mmol) was added dropwise, not to increase temperature over 20C. The solution was stirredat room temperature by 1 hour and it was slowly poured onto ice (50 g). The precipitate wasfiltered off, washed with water and added portionwise to the solution ofnatrium sulfite (7.5 g,60 mmol) in water (28 mL) at temp. 80C.The mixture was stirred at 90Cby 1 hour and 50% natrium hydroxide was slowly dropped to maintain pH= 8-9. Thehot mixture was filtered off and the filtrate was keep at room temperature for10 hours. The white crystals of product 4-chlorobenzenesulfinate natrium saltwas filtered off, washed by cold water and dried at room temperature. Product 3was obtained in 75% yield (4.3 g). IR (cm-1): 1575 (CHar); 1340,1130 (SO2); 1004, 981 (CH); 832, 740 (CCl).
With Sodium hydrogenocarbonate; anhydrous sodium sulphite; In water monomer; at 70 - 80℃; for 4h; General procedure: 4-Methoxybenzenesulfinic acid sodium salt (1j) was prepared by heating 2.5 g of sodium sulfite, 2.06 g of 4-methoxybenzenesulphonyl chloride, and 1.68 g of sodium bicarbonate in 9.6 mL of water at 70-80 C for 4 h. After cooling to room temperature, water was removed under vacuum and the residue was extracted by ethanol, recrystallization as a white solid, the yield was 67% (1.34 g). Similarly, other sodium arenesulfinates were prepared from their corresponding sulphonyl chlorides.
With sodium dihydrosulfite; Sodium hydrogenocarbonate; In water monomer; at 80℃; for 4h; General procedure: Sodium sulfite 3a-l (0.02mol), aryl sulfonyl chloride (0.01mmol), and sodium bicarbonate (0.02mol) were dissolved in distilled water (9.6mL). The reaction mixture was stirred at 80C for 4 hand then cooled to room temperature. Water was removed under vacuum and the residue was extracted by ethanol (25mL) to afford the desired aryl sulfinate with yield of 20%-80%.
With Sodium hydrogenocarbonate; anhydrous sodium sulphite; In water monomer; at 80 - 90℃; for 3h; General procedure: The substance was synthesized according to a previously reported procedure with some modifications.[3] To a stirred and warmed (80 oC) solution of Na2SO3 (2.36 g, 19 mmol) and NaHCO3 (1.68 g, 20 mmol) in 100 mL H2O was added portionwise arylsulfonyl chloride (10 mmol). The mixture was stirred at 90 C for 3 h, then filtered, and the filtrate concentrated under vacuum. The residue was recrystallised from water (5 mL) to yield the corresponding sodium arylsulfinate.
With Sodium hydrogenocarbonate; anhydrous sodium sulphite; In water monomer; at 70 - 80℃; for 4h;Inert atmosphere; General procedure: 4-Methoxybenzenesulfinic acid sodium salt (2e) was prepared by heating 2.5 g of sodium sulfite,2.06 g of 4-methoxybenzenesulphonyl chloride, and 1.68 g of sodium bicarbonate in 9.6 mL of waterat 70-80 C for 4 h. After cooling to room temperature, water was removed under vacuum and theresidue was extracted by ethanol, recrystallization as a white solid, the yield was 67% (1.34 g). Similarly,other sodium arenesulfinates were prepared from their corresponding sulfonyl chlorides.
With Sodium hydrogenocarbonate; anhydrous sodium sulphite; In water monomer; at 80℃; for 3h; General procedure: The ethyl 4-(chlorosulfonyl)benzoate (20 mmol, 1.0 equiv, 4.98 g) was dissolved in water (50 mL). Sodium sulfite (40 mmol, 2.0 equiv, 5.04 g) and sodium bicarbonate(40 mmol, 2.0 equiv, 3.4 g) were added, and the reaction mixture was stirred at 80 oCfor 3 h. The solvent was evaporated and ethanol (100 mL) was added to the residue.The suspension was heated to 80 oC for 10 min, refluxed and filtered. The filtrate wasevaporated, and then ethanol (100 mL) was added and heated to 80 oC for 10 min,refluxed and filtered at the second time. The solvent was evaporated under vacuum togive sodium 4-(ethoxycarbonyl)benzenesulfinate (1c, 2.7 g, 58%) as white powders.

References: [1]Patent: CN111793011,2020,A .Location in patent: Paragraph 0053; 0068-0071.
[2]Tetrahedron Letters,2014,vol. 55,p. 3851 - 3855.
[3]Chemistry - An Asian Journal,2016,vol. 11,p. 2121 - 2125.
[4]Journal of the American Chemical Society,2020,vol. 142,p. 10173 - 10183.
[5]European Journal of Organic Chemistry,2019,vol. 2019,p. 4179 - 4188.
[6]Acta chemica Scandinavica. Series A: Physical and inorganic chemistry,1976,vol. A30,p. 579 - 585.
[7]European Journal of Medicinal Chemistry,2007,vol. 42,p. 880 - 884.
[8]Patent: WO2007/66844,2007,A1 .Location in patent: Page/Page column 14-15.
[9]Journal of Physical Organic Chemistry,2010,vol. 23,p. 461 - 467.
[10]European Journal of Organic Chemistry,2014,vol. 2014,p. 3196 - 3202.
[11]Journal of Organic Chemistry,2014,vol. 79,p. 12018 - 12032.
[12]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 314 - 321.
[13]Tetrahedron,2014,vol. 70,p. 9107 - 9112.
[14]Chemical Communications,2015,vol. 51,p. 6418 - 6421.
[15]Green Chemistry,2016,vol. 18,p. 1874 - 1879.
[16]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2286 - 2292.
[17]Organic Letters,2016,vol. 18,p. 4144 - 4147.
[18]Chemical Communications,2017,vol. 53,p. 2056 - 2059.
[19]European Journal of Medicinal Chemistry,2018,vol. 160,p. 120 - 132.
[20]Tetrahedron Letters,2018,vol. 59,p. 4226 - 4230.
[21]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7959 - 7963.
[22]Molecules,2019,vol. 24.
[23]Chemistry - A European Journal,2019,vol. 25,p. 7259 - 7264.
[24]Chemical Communications,2019,vol. 55,p. 11864 - 11867.
[25]Journal of Organic Chemistry,2019,vol. 84,p. 13465 - 13472.
[26]Green Chemistry,2020,vol. 22,p. 2288 - 2300.
[27]Tetrahedron Letters,2021,vol. 64.
[28]Chemical Communications,2021,vol. 57,p. 2152 - 2155.
[29]Journal of the American Chemical Society,2021,vol. 143,p. 4903 - 4909.
[30]Organic and Biomolecular Chemistry,2021,vol. 19,p. 7066 - 7073.
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[34]European Journal of Organic Chemistry,2022,vol. 2022.
  • 3
  • [ 98-60-2 ]
  • [ 121148-00-3 ]
  • [ 121148-04-7 ]
  • 4
  • [ 83-73-8 ]
  • [ 98-60-2 ]
  • [ 784210-31-7 ]
  • 5
  • [ 2296-23-3 ]
  • [ 98-60-2 ]
  • 4-cyano-2-iodophenyl 4-chlorobenzenesulfonate [ No CAS ]
  • 6
  • [ 3337-66-4 ]
  • [ 98-60-2 ]
  • methyl 4-[(4-chlorophenyl)sulfonyl]oxy}-3,5-diiodobenzoate [ No CAS ]
  • 8
  • [ 24629-25-2 ]
  • [ 98-60-2 ]
  • [ 152338-16-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; at 40℃; for 8 - 12h; To a solution of (S) -isoleucinol (17.6 mg, 0.15 mmol) in CH3CN (600 muL) was added Et3N (300 I1L, 1M in CH3CN) and 4-CHLOROBENZENESULFONYL chloride (21.07 mg, 0.1 mmol) as a solution in CH3CN (400 1L). The vial was capped and shaken for 8 to 12 hours at 40 °C. The solvent was removed, and the oil was dissolved in EtOAc (1 mL). The resulting solution was washed with 1M HC1 (2 x LML). The solvent was removed in vacuo, and the residue dissolved in 1.6 ML DMSO (0.03 M).
With triethylamine; In acetonitrile; at 25℃; for 0.5h; To a solution OF 4-CHLOROBENZENESULFONYL chloride (1.93 g, 9.1 mmol) in CH3CN (25 mL) and (S) -isoleucinol (1.07 g, 9.1 mmol) was added Et3N (1.91 mL, 13.7 mmol). The reaction mixture was stirred at 25 °C for 30 minutes. The solvent was removed and the oil was dissolved in CH2C12 (20 mL). The solution was washed with water (2 x 20 mL) and dried over NA2S04. The solvent was removed to give N-4- chloro benzenesulfonyl isoleucinol, which was carried on without further purification.
  • 9
  • [ 98-60-2 ]
  • [ 68050-37-3 ]
  • 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In water; Example 20 4-Chloro-N-(5-chloroquinolin-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119 mg, Preparation Example 2) at room temperature. After stirring at room temperature for 3 days, water was added thereto and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, the resulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR (CDCl3) delta (ppm): 6.96 (1H, d, J=9.7 Hz), 7.34 (1H, d, J=8.4 Hz), 7.42-7.48 (3H, m), 7.54 (1H, t, J=8.4 Hz), 7.94 (2H, d, J=6.3 Hz), 8.29 (1H, d, J=9.7 Hz).
With pyridine; In water; Synthetic Example 20b 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119 mg, Production Example 2b) at room temperature, followed by stirring at room temperature for 3 days. Then, water was added thereto, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, theresulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR(CDCl3) delta(ppm): 6.96(1H,d,J=9.7Hz), 7.34(1H,d,J=8.4Hz), 7.42-7.48(3H,m), 7.54(1H,t,J=8.4Hz),7.94(2H,d,J=6.3Hz), 8.29(1H,d,J=9.7Hz).
With pyridine; In water; SYNTHETIC EXAMPLE 20b 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119mg, Production Example 2b) at room temperature, followed by stirring at room temperature for 3 days. Then, water was added thereto, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, the resulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.7 Hz), 7.34(1H, d, J=8.4 Hz), 7.42-7.48(3H, m), 7.54(1H, t, J=8.4 Hz),7.94(2H, d, J=6.3 Hz), 8.29(1H, d, J=9.7 Hz).
  • 10
  • [ 23687-26-5 ]
  • [ 347145-20-4 ]
  • [ 98-60-2 ]
  • [ 937-14-4 ]
  • [ 347146-91-2 ]
YieldReaction ConditionsOperation in experiment
In chloroform; Synthetic Example 84b 6-(4-Chlorobenzenesulfonylamino)-1-cyanoisoquinoline The compound obtained using <strong>[23687-26-5]6-aminoisoquinoline</strong> (0.5 g, Synthesis, 733 (1975)) and 4-chlorobenzenesulfonyl chloride (0.88 g) in the same method as in Synthetic Example 1b was dissolved in chloroform (150 ml). Under ice-cooling, m-chloroperbenzoicacid (0.9 g) was added theterto, followed by stirring at room temperature overnight. The solvent was evaporated, and the resulting crystals were washed with diethyl ether, collected by filtration and dried, to give 6-(4-chlorobenzenesulfonylamino)isoquinoline-N-oxide (1.072 g).
  • 11
  • [ 37585-16-3 ]
  • [ 98-60-2 ]
  • [ 922711-38-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In chloroform; at 20℃; for 5h; A solution of <strong>[37585-16-3](2-amino-4-chlorophenyl)methanol</strong> (5.00 g, 31.85 mmol) and pyridine (3.1 mL) in anhydrous chloroform (150 mL) was treated dropwise with a solution of 4- chlorobenzenesulfonyl chloride (7.26g ,34.58 mmol) in chloroform (30 mL) over 20 minutes at room temperature. The reaction mixture was stirred for 5 hours and evaporated to dryness. The resulting residue was taken up in ethyl acetate (200 mL) and aqueous ammonium chloride (100 mL). After stirring for 30 minutes the organic phase was separated and further washed with dilute ammonium chloride (2 x 50 mL), dried EPO <DP n="29"/>over sodium sulfate, filtered and evaporated to give an oil. This was triturated in hot hexane (10OmL) and then stirred at ambient temperature for 2 hours. The solid was collected and washed with hexane to give the title compound (10.0 g). HPLC Rt = 3.04 minutes. 1H NMR (CDCI3) delta 7.75 (d, 2H), 7.53 (s, 1H), 7.45 (d, 2H), 7.09 (dd, 1 H), 7.01 (d, 1 H), 4.40 (s, 2H).
  • 12
  • N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide [ No CAS ]
  • [ 98-60-2 ]
  • [ 350800-81-6 ]
  • [ 1185265-17-1 ]
YieldReaction ConditionsOperation in experiment
In pyridine; 4-Chloro-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-chloro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=264-266 C, (M+H)+=508.
  • 13
  • [ 98-60-2 ]
  • [ 350800-81-6 ]
  • N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; 4-Chloro-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-chloro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=264-266 C, (M+H)+=508.
  • 14
  • [ 4771-49-7 ]
  • [ 98-60-2 ]
  • [ 1356239-96-7 ]
YieldReaction ConditionsOperation in experiment
91.93% With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 5℃; for 2h; Add III-3 (1.00g, 6.29mmol), DMAP (154mg, 1.26mmol), DIEA (3.12mL, 18.87mmol) to 100mL three-necked flask, stir and dissolve with 10mL acetonitrile, slowly add at 05C 4-chlorophenylsulfonyl chloride (IV-5, 1.60g, 7.55mmol) in 10mL acetonitrile solution, after the addition was completed, stirring was continued for 2 hours under low temperature conditions.TLC monitoring of raw material reactionsCompletely, concentrate the reaction solution, dissolve with 30 mL of ethyl acetate, wash with 40 mL of water, and then extract twice with ethyl acetate (20 mL×2). The organic phase is combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate The filtrate is spin-dried and subjected to column chromatography (petroleum ether:Ethyl acetate = 10:1 rinse),After drying, 1.71 g of a brownish yellow solid V-11 was obtained.The yield was 91.93%.
  • 15
  • [ 1455-20-5 ]
  • [ 98-60-2 ]
  • 2-n-butyl-4-(4-chlorophenyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.7% With bis(benzonitrile)palladium(II) dichloride; tributylphosphine; 25,26,27,28-tetrakis(hydroxy)calix[4]arene; sodium carbonate; In 1,4-dioxane; at 90℃; for 24h;Inert atmosphere; Added to the synthesis reactor 1mmol formula (I) compounds and 1.8mmol compound of formula (II), then adding 5 ml solvent 1,4-dioxane and 8mmol sodium carbonate, stirring, add 0.09mmolPd (PhCN)2Cl 2 and 75 mg mass ratio of 1 : 0.8 cup [4] arenes and tributylphosphine additive mixture, and then carry on argon-vacuum suction replacement three times, and then sealing the stirring and gradually raising the temperature to 90 C reaction 24h, after the reaction cooled to room temperature, mixed solution by filtration, after the spin vaporization, the silica gel column chromatography purification, the compounds of formula (III) can be obtained, the yield of 98.7%, purity of 98.5% (HPLC)
  • 16
  • [ 58196-33-1 ]
  • [ 98-60-2 ]
  • [ 1562444-15-8 ]
YieldReaction ConditionsOperation in experiment
87% With pyridine; In tetrahydrofuran; at 0℃; for 4h; To a solution of <strong>[58196-33-1]1,2,3,4-tetrahydroquinolin-7-ol</strong> (4.68g, 31.4mmol, Astatech) and pyridine (3.04mL, 37.6mmol) in THF (30mL) at 0C was added a solution of 4-chlorobenzene-1-sulfonyl chloride (6.95g, 32.9mmol) in THF (15mL) dropwise. The reaction was stirred at 0C for 4h. The reaction mixture was concentrated with silica gel and purified by flash chromatography (10-40% EtOAc in hexanes) to give 49 (8.8g, 87%) as a pale-yellow solid. 1H NMR (400MHz, chloroform-d) delta ppm 7.54-7.58 (2H, m), 7.37-7.41 (2H, m), 7.36 (1H, d, J=2.5Hz), 6.89 (1H, d, J=8.4Hz), 6.64 (1H, dd, J=8.4, 2.5Hz), 3.76-3.82 (2H, m), 2.40 (2H, t, J=6.7Hz), 1.57-1.65 (2H, m). MS ESI (pos.) M/E: 324 (M+H).
  • 17
  • [ 58196-33-1 ]
  • [ 98-60-2 ]
  • [ 1562443-03-1 ]
  • 18
  • [ 138588-22-4 ]
  • [ 98-60-2 ]
  • 4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20.0℃; for 16.0h; 3-(Pyridin-2-yl)- 1 ,2,4-thiadiazol-5-amine (50 rag, 0.28 mmoi) was dissolved in 1.5 ml, pyridine. 4-Chlorobenzenesulfonyl chloride (65 mg, 0.31 mmol) was then added. The mixture was stirred for 16 hours at room temperature. The reaction was partitioned between dichloroniethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to obtain Compound 14 as a tan solid. LCMS (M/Z): 352 (M + H). NMR (400 MHz, acetone) delta ppm 7.53 - 7.63 (m, 3 H) 7.91 (d, J 8.64 Hz, 2 H) 8.03 (td, J=7.75, 1.54 Hz, 1 H) 8.24 (d, J 8.00 Hz, 1 IT) 8.66 (d, J 4.49 Hz, 1 H).
  • 19
  • [ 858854-82-7 ]
  • [ 98-60-2 ]
  • C12H7Cl2IO3S [ No CAS ]
  • 20
  • [ 98-60-2 ]
  • [ 92914-74-4 ]
  • 4-chloro-N-isoxazolo[5,4-b]pyridin-3-yl-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; In tetrahydrofuran; at 60 - 65℃; for 0.25h;Microwave irradiation; General procedure: To a solution of <strong>[92914-74-4]3-aminoisoxazolo[5,4-b]pyridine</strong>(1) (1.35 g, 0.01 mol) in 100 mL of tetrahydrofurane tetrahydrofurane,a few drops of anhydrous pyridine and 0.01mol of the appropriate arylsulfonyl chlorides: benzene-,4-bromobenzene-, 4-chlorobenzene-, ptoluene-and 4-methoxybenzenesulfonyl chlorideswere added. The reaction mixture was heated underreflux while being stirred in the microwave reactorin an aluminum bath at 60-65OC for 15 min (3 5min with 5 min breaks) at microwave power P = 240W. The solvent was evaporated under vacuum andthe residue obtained was triturated with water, filtered,dried and crystallized from ethanol.
  • 21
  • [ 98-60-2 ]
  • [ 92914-74-4 ]
  • 4-chloro-N-[(4-chlorophenyl)sulfonyl]-N-(isoxazolo[5,4-b]pyridin-3-yl-)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With pyridine; In tetrahydrofuran; at 60 - 65℃; for 0.25h;Microwave irradiation; General procedure: To a solution of <strong>[92914-74-4]3-aminoisoxazolo[5,4-b]pyridine</strong>(1) (1.35 g, 0.01 mol) in 100 mL of tetrahydrofurane,a few drops of anhydrous pyridine and 0.02mol of the appropriate arylsulfonyl chlorides: benzene-,4-bromobenzene-, 4-chlorobenzene- and 4-methylbenzenesulfonyl chlorides were added. Thereaction mixture was heated under reflux whilebeing stirred in the microwave reactor in an aluminumbath at 60-65OC for 15 min (3 5 min with5 min breaks) at microwave power P = 240 W. Thesolvent was evaporated under vacuum and theresidue obtained was triturated with water, filtered,dried and recrystallized from ethanol.
  • 22
  • [ 6174-86-3 ]
  • [ 98-60-2 ]
  • 3-chloro-4-methyl-2-oxo-2H-chromen-7-yl 4-chlorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In tetrahydrofuran; at 20℃; for 4h; General procedure: Coumarin sulfonates 1-38 were synthesized by reactingdifferent hydroxylated coumarin derivatives (1 mmol) withcommercially available sulfonyl chlorides derivatives (1.2 mmol) inTHF (15 mL) and triethyl amine (1 mmol) was used as base. Reactionmixture was stirred for 4 h at room temperature to afford avariety of coumarin sulfonate esters 1e38. TLC monitoring wasused to determine the progress of the reaction. After the completionof reaction, THF was evaporated under reduced pressure andthe solid product obtained was washed with distilled water anddried under vacuum. The products were recrystallized in methanoland gave good yields. All the synthetic compounds 1-38 werecharacterized by different spectroscopic techniques such as EI-MS,HREI-MS, 1H-NMR, and 13C-NMR.
  • 23
  • [ 20358-03-6 ]
  • [ 98-60-2 ]
  • N-(5-bromobenzo[d]thiazol-2-yl)-4-chlorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With pyridine; In dichloromethane; at 0 - 20℃; for 16h; To a solution of intermediate 99-i in DCM (0.5 M) at 0°C was addedchlorobenzenesulfonylchloride (1.2 eq) and pyridine (2.0 eq). The reaction was allowed to warm to rt and stirred for 16 h. The solution was concentrated under reduced pressure and the residue was taken up in saturated NaHCC>3. The resulting mixture was extracted with 2x 10 mL EtOAc and the combined organics were washed with saturated NaHCC>3, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The1 crude material could be purified by recrystallization from DCM (35 mg, 36percent). H NMR(400 MHz, DMSO-de) delta 11.06 (s, 1H), 7.83 (d, J = 8.6 Hz, 2H), 7.78 - 7.61 (m, 3H), 7.47 (d, J = 2.4 Hz, 1 H), 7.28 (dd, J = 8.8, 2.4 Hz, 1 H).
  • 24
  • [ 98-60-2 ]
  • [ 56293-29-9 ]
  • 12N-p-chlorobenzenesulfonyl aloperine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate; In dichloromethane; at 0 - 20℃; General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee.
  • 25
  • [ 1080-12-2 ]
  • [ 98-60-2 ]
  • (E)-2-methoxy-4-(3-oxobut-1-enyl)phenyl 4-chlorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine; In methanol; at 20℃; General procedure: Solutions of selected methyl ketones (2 mmol) in methanol(6 mL) were stirred and corresponding sulfonylchlorides (2.4 mmol) were added. Then, triethylamine(0.6 mL) was added dropwise. The mixtures were stirredovernight at room temperature. After completion of thereactions, mixtures were poured into iced water withstirring. In some cases (for our compounds 7f, 7g, 8e, 8f,8g, and 9g; see below), the formed precipitate was filteredand washed with cold diethyl ether. In other cases, whenno precipitate formed, the organic layer was extractedwith dichloromethane (3 × 50 mL), dried over anhydrousNa2SO4 and evaporated under vacuum. The residue waspurified by short column chromatography on silica gel,using dichloromethane as eluent. The oil obtained usuallycrystallized; if not, the oily residue was dissolved indiethyl ether from which products crystallized on standingin a deepfreeze. Crude products were washed with coldether, and 21 pure, mostly white crystals were obtained, asfollows:
  • 26
  • [ 98-60-2 ]
  • [ 5294-61-1 ]
  • 2-(4-((4-chlorophenyl)sulfonyl)piperazin-1-yl)-N-(2,6-dimethylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In dichloromethane; at 25℃; for 8.0h; General procedure: An equimolar mixture of N-(2,6-dimethy lphenyl)-2-(piperazin-1-yl)acetamide 4 (0.001 mol) and different substituted benzene sulfonyl chlorides 5a-e (0.001 mol) in methylene dichloride were stirred for about 8 h in presence of triethylamine at 25oC. The completion of the reaction was checked by TLC. Then it was poured into ice-cold water and extracted with MDC. The organic layer was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get piperazine sulphonamide derivatives 6a-e in high yield.
 

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