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[ CAS No. 161798-01-2 ] {[proInfo.proName]}

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Chemical Structure| 161798-01-2
Chemical Structure| 161798-01-2
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Product Details of [ 161798-01-2 ]

CAS No. :161798-01-2 MDL No. :MFCD13194810
Formula : C14H13NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :NJRGQNNSIAFIJC-UHFFFAOYSA-N
M.W : 291.32 Pubchem ID :135404723
Synonyms :

Calculated chemistry of [ 161798-01-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.21
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.01
TPSA : 104.73 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.67
Log Po/w (XLOGP3) : 3.23
Log Po/w (WLOGP) : 2.81
Log Po/w (MLOGP) : 0.96
Log Po/w (SILICOS-IT) : 4.08
Consensus Log Po/w : 2.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.76
Solubility : 0.0508 mg/ml ; 0.000175 mol/l
Class : Soluble
Log S (Ali) : -5.1
Solubility : 0.0023 mg/ml ; 0.0000079 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.05
Solubility : 0.0261 mg/ml ; 0.0000897 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.07

Safety of [ 161798-01-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 161798-01-2 ]

* 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 [ 161798-01-2 ]

[ 161798-01-2 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 78-77-3 ]
  • [ 161798-01-2 ]
  • [ 161798-03-4 ]
YieldReaction ConditionsOperation in experiment
94.7% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 75 - 85℃; for 6h; In a 500 ml round bottom flask, 129 g of DMF, 17 g (0.058 mol) of ethyl 2-(3-aldehyde-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, 32.24 g (0.233) were added. Potassium carbonate and 0.2 g of potassium iodide.An additional 20 g (0.146) of isobutyl bromide (FBT-SM2) was added.After the addition, the temperature was raised to 75-85 C for 6 h.After the reaction is completed, the temperature is lowered to 20 to 30 C.136 g of purified water was added to the reaction vessel and incubated at 20 to 30 C for 1 h.After the heat preservation, filtration, the filter cake was beaten with purified water, and the pH of the beater was 10, filtered and dried to obtain 21.5 g of 2-(3-formyl-4-isobutoxy-phenyl)-4-methyl-thiazole. Crude product of -5-ethyl formate (FBT-1).In a 500 ml round bottom flask, 67 g of ethanol, 102 g of formic acid and 21.5 g of ethyl 2-(3-formyl-4-isobutoxy-phenyl)-4-methyl-thiazole-5-carboxylate (FBT-) were added. 1) The crude product is stirred and heated to 60-70 C, and after cooling, the temperature is lowered to 15-30 C for 1 h, the crystallization is completed, filtered and dried to obtain 19.2 g of 2-(3-formyl-4-isobutoxy) -Phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (FBT-1), refined 89.3%, total yield 94.7%, intermediate content 98.40%, maximum single impurity less than 0.10%.
90% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 8h; 250 ml of N,N-dimethylformamide was added to the reaction flask. Add 50g in sequence with stirring Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl-thiazole-5-carboxylate, 58.78 g of bromoisobutane, Then add 71.16g of anhydrous potassium carbonate, and the feeding is completed. Heat to 80 C for about 8 h. Yellow turbid. TLC detects the reaction completely and drops to room temperature. Continue to drop to 0 C, add ice water to quench, violent exotherm, Slowly add ice water, the reaction solution becomes viscous, and stirring is continued for 30 minutes. After suction filtration, the vessel was washed with an appropriate amount of water and dried to obtain a solid 56.7 g. The yield is 95.1%, and the purity is 98.2%. The product obtained is further purified: a mixture of EA and PE is arranged, The obtained product and the mixed solution were mixed and beaten for 1 hour. Then filter and dry, wherein the EA:PE volume ratio is 2:1, Solid: total liquid volume = 1g: 6ml, The purity of the product obtained after purification was 99%, and the yield was about 90%.
83% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 70℃; for 4h;Product distribution / selectivity; Example 6 - Preparation of Compound of formula III)[0094] A compound of formula II (10.0 gr, 34.33 mmol) was reacted with iso- butyl bromide (18.9 gr, 137.3 mmol) in the presence of potassium carbonate (19.0 gr, 137.3 mmol) and potassium iodide (2.3 gr, 13.7 mmol) in 60 ml dimethylformamide. The reaction was performed at about 70C during 4 hours. The reaction mixture was extracted at 70C using 300 ml ethyl acetate and 600 ml water. The separated aqueous phase was washed twice with 100 ml ethyl acetate. The combined organic phase was washed twice with 100 ml water and then concentrated to dryness. The resulting solid residue was re- crystallized from 70 ml ethyl acetate, filtered and dried under reduced pressure at about 40C to provide a compound of formula III (8.9 gr, yield - 83%). The Compound of formula III purity is 99.1% (by HPLC).
To a stirred solution of ethyl 2-[3-formyl-4-hydroxyphenyl]-4-methylthiazole-5- carboxylate (10 gms) in dimethylformamide (40 ml) added potassium carbonate (9.78 gms) and potassium iodide (2.35 gms). Heated the reaction mixture to 70 - 75C and stirred for 30 minutes. To the above reaction added a solution of l-bromo-2- methylpropane (9.72 gms) in dimethyl formamide (10 ml) and stirred for 5 hours. Cooled the reaction mixture to 25C, quenched with water and stirred for one hour. Filtered the precipitated solid and dried the material to get the title compound. Yield: 9 gms.
With potassium carbonate; N,N-dimethyl-formamide; at 87 - 93℃; for 4h; b) Preparation of Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate [Compound of formula IV1.350.0gm of Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate, [Compound of formula III] 332. Ogm of potassium carbonate and 330.0gm of isobutyl bromide were added to 1.751tr of DMF. Reaction mixture was heated to 90 +/- 3C and stirred for 4 hr. Reaction mixture was cooled to 25C and slowly added 10.50 ltr of water. Slurry of the product formed was stirred for 2.0hr, filtered, washed and dried under vacuum to give 389 gm of titled compound.Analytical Data- · ^NMR (CDC13, 400 MHz) : delta 1.079-1.101 (doublet, 6H); delta 1.366-1.413 (triplet,3H); delta 2.185-2.230 (multiplet, 1H); delta 2.769 (singlet, 3H); delta 3.914-3.935 (doublet, 2H); delta 4.316-4.387 (quartet, 2H); delta 7.045-7.074 (doublet, 1H); delta 8.188-8.225 (doublet of doublet, 1H); delta 8.353-8.361 (doublet, 1H).? Mass (m/e): 348.3
With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 25 - 85℃; for 5.08333h; Example 3:Preparation of 2-(3-formyl-4-isobutoxyphenyI)-4-methyIthiazole-5-carboxylic acid ethyl esterTo a dimethylformamide (1250 ml) was added 2-(3-formyl-4-hydroxyphenyl)-4- methylthiazole-5-carboxylic acid ethyl ester (250 gm) at room temperature for 5 minutes to obtain a solution. To the solution was added potassium carbonate (250 gm) and potassium iodide (62.5 gm), and then added isobutyl bromide (100 gm) slowly for 2 hours. The temperature of the reaction mass was raised to 85C and maintained for 3 hours. The dimethylformamide solvent was distilled off under vacuum at 80C and then cooled to room temperature. The reaction mass was added water (2500 ml) and stirred for 2 hours at room temperature. The separated solid was filtered, washed with cycloheaxne and then dried to obtain 285 gm of 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5- carboxylic acid ethyl ester.
16.43 g With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 4h; Dissolve 14.14g of <strong>[161798-01-2]ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate</strong> (Formula III) in 55 ml dimethylformamide, at ambient temperature. Add 40g of potassium carbonate, along with 15.9 ml isobutyl bromide. Heat the reaction to 75-80 C and stir for 4 hours. Cool to 25-30 C, while 165 ml process water is added. Further cool to 0-5 C and stir for 30 minutes at this temperature. Filter off the precipitated solid and wash the filter cake with 55 ml process water. The wet cake is dried under vacuum at 40 C for 7 hours, to furnish 16.43 g of ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (Formula lib). of compound of formula Illb
34.2 g With potassium carbonate; In N,N-dimethyl-formamide; at 60 - 115℃; Formylation reaction is complete, no need to separate,Continue the next isobutylation reaction,DMF as the reaction solvent,164g of dimethylformamide was added, dissolved,Then add 14g potassium carbonate,21.7g bromoisobutane was added dropwise, the reaction was warmed,The reaction temperature is controlled at 60-115 C,The reaction time is 3-10 hours, the reaction was completely detected by HPLC,Slowly dropping 76g of water,Cooled to room temperature filtered, centrifuged,Centrifuge the filter cake first with 50g DMF (dimethylformamide) once, high-speed spin-dry;Then washed with 19g of water for the first time,High-speed centrifuge drying, washing with 19g water a second time,High-speed centrifuge drying;Finally, the first wash with 15g methanol,High-speed centrifuge drying, washed with 15g methanol second time,High-speed centrifuge drying;The wet product was dried to give 34.2 g of ethyl 2- (3-aldehyde-4-isobutyloxyphenyl) -4-methylthiazole-5-Chromatographic purity of 99.2%Content of 99.5%, two-step total yield of 68.2%.
With triethylamine; at 75℃; for 15h;Large scale; Add 400 kg of DMAC, 100 kg of 2- (3-formyl-4-hydroxyphenyl) -4-methylthiazole-5-carboxylic acid ethyl ester to the reaction tank,50kg bromoisobutane, 35kg triethylamine,The temperature was raised to 75 C for 15h.Then, 25 kg of hydroxylamine hydrochloride was added at a reduced temperature, and reacted at 75 C for 3 hours.Then 30 kg of acetyl chloride was added dropwise and reacted at 80 C for 7 hours.After the reaction was completed, the temperature was lowered to 20-30 C, water was added, 20 kg of sodium hydroxide was added, and hydrolysis was performed at 45 C for 6 hours.Then add hydrochloric acid dropwise to adjust the pH to 6.0-7.0. Reduce the temperature to 0-5 C, then add water and crystallize for 2h.After centrifugation, a white solid powder was obtained, and the obtained powder was crude febuxostat with a wet weight of 128 kg.

  • 2
  • [ 78-77-3 ]
  • [ 161798-01-2 ]
  • [ 1271738-74-9 ]
YieldReaction ConditionsOperation in experiment
73% Example 13 - Preparation of Compound of formula Vl-a[00101] A compound of formula II (10.0 gr, 34.33 mmol) was reacted with iso- butyl bromide (18.9 gr, 137.3 mmol) in the presence of potassium carbonate (19.0 gr, 137.3 mmol) and potassium iodide (2.3 gr, 13.7 mmol) in 100 ml dimethylformamide. The reaction was performed at about 70°C during 4 hours. Hydroxylamine hydrochloride (Then 3.6 gr, 51.8 mmol) was then added at about 70°C and stirred at this temperature during 7 hours. The reaction mixture was diluted with 80 ml toluene, 100 ml water was added and the mixture was allowed for the phase separation. The organic phase was washed first time with 100 ml water and second time with 50 ml water at about 70°C, cooled to about 55°C, stirred at this temperature during 1 hour to deepen precipitation and then cooled to about 10°C, filtered, washed with 10 ml toluene and dried under reduced pressure at about 40°C to provide a compound of formula Vl-a (8.2 gr, yield - 73percent). The Compound of formula Vl-a purity is 96.4percent (by HPLC).
  • 3
  • [ 161798-01-2 ]
  • febuxostat [ No CAS ]
  • 5
  • [ 161798-01-2 ]
  • [ 144060-62-8 ]
  • 6
  • [ 161798-01-2 ]
  • [ 1271738-74-9 ]
  • 7
  • [ 161798-01-2 ]
  • [ 1350352-70-3 ]
  • 8
  • [ 161798-01-2 ]
  • [ 1350352-71-4 ]
  • 9
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  • [ 1350352-72-5 ]
  • 10
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  • [ 1350352-73-6 ]
  • 11
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  • [ 1350352-74-7 ]
  • 12
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  • [ 1350352-75-8 ]
  • 13
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  • [ 1350352-76-9 ]
  • 14
  • [ 609-15-4 ]
  • [ 161798-01-2 ]
  • 15
  • [ 161797-99-5 ]
  • [ 100-97-0 ]
  • [ 161798-01-2 ]
YieldReaction ConditionsOperation in experiment
81.3% A method for controlling the impurity of non-bupretane intermediate is as follows:To 200L clean and dry reactor into the polyphosphoric acid 120kg,Stirring heated to 40 ~ 50 ,Stir with the sameWas added 20 kg (76.0 mol) of ethyl 2- (4-hydroxyphenyl) -4-methyl-5-thiazolecarboxylate 11 kg (76.3 mol)HMTA (urotropine, chemical name hexamethylenetetramine)The Plus finished,Heating up to 93 ° C,Reaction 3h,(4-hydroxyphenyl) -4-methyl-5-thiazolecarboxylic acid ethyl ester,Stop the reaction.The reaction ends,The reaction solution was added to the ice aqueous solution of dilute acetic acid,Hydrolyzed for 20 minutes,Extracted with ethyl acetate 300 L three times,Combined organic phase,Plus 10kg yuan Ming powder dry,filter,The filtrate was concentrated under reduced pressure to give 210 mg of solvent ethyl acetate.To the concentrate was added 100 kg of water,Stirring crystallization,Centrifugal,dry,To obtain a light yellow non-cloth he intermediate 18.0 kg.Yield 81.3percent.Intermediate 2- (3-formyl-4-hydroxyphenyl) -4-methyl-5-thiazolecarboxylic acid ethyl ester Content 99.4percent, dicarboxylic acid impurity content0.008percent
72.3% With methanesulfonic acid; at 75℃; for 10h; Example 2: Synthesis of Ethyl-2-(3-Formyl-4-HvdroxyphenvD-4-Methyl-5-Thiazole CarboxylateHexamethylene tetramine (134 g, 0.971 mol) was added to a solution of ethyl 2-(4- hydroxyphenyl)-4-methyl-5-thiazol carboxylate (100 g, 0.38 mol) in methanesulfonic acid (500 mL) slowly over a period of about 30 minutes. The reaction mixture was heated to about 75°C and stirred for about 10 hours. After completion of reaction, the reaction mixture was cooled to about 30°C and water was added to it. The reaction mixture was further cooled to about 0°C and stirred for about 1 hour. The solid thus obtained was filtered, washed with water and dried to give the title compound. (Yield: 80 g, 72.3percent)
With trifluoroacetic acid; for 40h;Reflux; a) Preparation of Ethyl 2-(3-formyl-4-hvdroxyphenyl)-4-methyl-5-thiazolecarboxylate[Compound of formula lO.Ogm of Ethyl 2-(4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate, [Compound of formula II] and 5.86gm of hexamethylenetetramine was added to 100.0ml of trifluoroacetic acid. Reaction mixture was heated to reflux under stirring for 40 hr. Trifluoroacetic acid was distilled out at 80 +/- 3°C. Residue obtained was cooled to 25°C and slowly added 100 ml of water. Slurry formed was stirred for 2.0hr. Slurry of the product was filtered, washed and dried under vacuum to give 9.6 gm of titled compound.
Example 2:Preparation of 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester2-(4-Hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (413 gm) was added to trifluoroacetic acid (2065) and then added hexamethyl tetramine (248 gm) at room temperature. The contents were heated to 80 C and maintained for 24 hours. The reaction mass was then cooled to room temperature and mass was poured into child water (5155 ml). The reaction mass was extracted with toluene (2887 ml) and stirred for 10 minutes. Then the layers were separated and the aqueous layer was extracted with toluene. Combined organic layers were dried with sodium sulfate and then concentrated to obtain a residual solid. To the residual solid was added cyclohexane (1250 ml) at room temperature and then heated to reflux for 30 minutes. The reaction mass was then cooled to room temperature and stirred for 1 hour. The solid obtained was collected by filtration and dried to obtain 260 gm of 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5- carboxylic acid ethyl ester.
4-Hydroxybenzo-thioamide (1.0 mmol), IPA (10 mL) and ethyl-2-chloro acetate (1.1 mmol) was heated to 75°C. After completion of reaction, the mixture was poured into water, filtered and washed with water to neutral pH and recrystallized from IPA to give the compound 1. The ethyl 2-(4-hydroxyphenyl)-4-methyl-thiazole-5-carboxylate 1 (1.0 mmol) after adding PPA (10.0 mmol) was heated to 75°C and then HMTA (2.6 mmol) added at 75°C. After the completion of reaction, the reaction mass was poured onto aqueous acetic acid solution and stirred for a few minutes at RT and the obtained product was filtered and washed with water at RT. The final intermediate ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate 2 was purified by recrystallization from IPA.
With sulfuric acid; at 60 - 120℃; In a clean reaction flask,Put 170g polyphosphoric acid,10g sulfuric acid,22.3 g hexamethine tetramethylammonium,38 g of ethyl 2- (4-hydroxyphenyl) -4-methyl-5-thiazolecarboxylate (Formula III)Control the reaction temperature is 60-120 ,The reaction time is 3-10 hours,HPLC detection reaction was complete,234 g of butyl acetate and 126 g of water were added,Stirring, standing, stratification,The organic layer was added 76g of water (can be used for the next batch of application) stirring, standing, delamination,The organic layer was concentrated to dryness to give ethyl 2- (3-carboxyphenyl-4-hydroxyphenyl) -4-methyl-5- thiazolecarboxylate (Formula IV)

  • 17
  • [ 161798-01-2 ]
  • [ 161798-02-3 ]
YieldReaction ConditionsOperation in experiment
99% Example - 2: Preparation of Ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl thiozole - 5-carboxylateA mixture of 10. Og of Ethyl-2-(3-formyl-4-hydroxy phenyl)-4-methyl thiozole -5- carboxylate and 2.85 g of hydroxylamine hydrochloride were stirred for 30 minutes in 30 g of Dimethylformamide. To this reaction mixture 3.3 grams of acetyl chloride was added and stirred at 90°C for 2-3 hours. Reaction mass was cooled to room temperature and diluted with 100 ml of water and stir for 2 hours. The reaction mass was filtered and washed with purified water to give 10.0 g of Ethyl-2-(3-cyano-4-hydroxy phenyl)-4- methyl thiozole -5-carboxyltae (yield 99.0percent).
99.0% Example-2 Preparation of Ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl thiozole-5-carboxylate A mixture of 10.0 g of Ethyl-2-(3-formyl-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate and 2.85 g of hydroxylamine hydrochloride were stirred for 30 minutes in 30 g of Dimethylformamide. To this reaction mixture 3.3 grams of acetyl chloride was added and stirred at 90° C. for 2-3 hours. Reaction mass was cooled to room temperature and diluted with 100 ml of water and stir for 2 hours. The reaction mass was filtered and washed with purified water to give 10.0 g of Ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate (yield 99.0percent).
97.6% With formic acid; hydroxylamine hydrochloride; sodium acetate; at 100 - 105℃; for 10h; In a 1 L four-necked flask, 60 g of a non-Bustam aldehyde substrate, 866.7 g of anhydrous formic acid, 17.3 g of hydroxylamine hydrochloride and24g anhydrous sodium acetate, stirring warming. The temperature of T = 100 ~ 105 , heat stirring 10h, the material vacuum distillation to no distillate to get the powdery solid compound . Weighing 86.8g, molar yield 97.6percent, purity (HPLC): 98.9percent, single impurity (HPLC): 0.22percent, total miscellaneous (HPLC): 1.1percent.
85.9% With formic acid; hydroxylamine hydrochloride; sodium formate; at 100℃; for 8h; Example 3: Synthesis of ethyl-2-(3-cyano-4-hvdroxyphenvn-4-methyl-5-thiazole carboxylateHydroxylamine hydrochloride (35.82 g, 0.515 mol) and sodium formate (46.73 g, 0.687 mol) were added to a solution of ethyl-2-(3-formyl-4-hydroxyphenyl)-4-methyl-5- thiazole carboxylate (100 g, 0.343 mol) in formic acid (anhydrous, 300 mL) and the reaction mixture was heated to a temperature of about 100°C for about 8 hours. After completion of reaction, the reaction mixture was cooled to about 40°C and water was added to it. The reaction mixture was cooled to about 25°C and stirred for about 1 hour. The solid obtained was filtered, washed with water and dried. The solid was then dissolved in acetone at about 50°C and water was added slowly over a period of about 30 minutes. The mixture was cooled to about 25°C and again stirred for about 1 hour. The solid thus obtained was filtered, washed with acetone:water (1 :1) mixture and dried to obtain the title product. (Yield: 85 g, 85.9percent)
42.6% With ammonia; iodine; In tetrahydrofuran; water; at 25 - 30℃; In a 50 mL round-bottomed flask charge under stirring 0.5g (1.72 mmol) of ethyl 2-(3-formyl-4- hydroxyphenyl)-4-methylthiazole-5-carboxylate in 8.6 mL THF, at 25-30 °C. Add 10.3 mL (544.94 mmol) 25percent aqueous ammonia, under stirring at 25-30 °C. Add 480 mg (1.89 mmol) iodine (I2) to the reaction mass, stir the reaction mixture at 25-30 °C for 15-30 min. Check the progress of the reaction by TLC (cyclohexane: ethyl acetate 1 :1). Starting material is consumed. Add 8.6 mL 5percent w/v aqueous thiosulfate and 40 mL ethyl acetate at the reaction mass, separate organic layer and extract aqueous layer twice with 40 mL ethyl acetate. Combine organic layers, dry over anhydrous sodium sulfate, filter off and concentrate to dryness. Purification of the residue with column chromatography (cyclohexane: ethyl acetate 3: 1) afforded 0.213 g of ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate (Formula Ilia). Yield : 42.6percent.

  • 18
  • [ 78-77-3 ]
  • [ 161798-01-2 ]
  • [ 160844-75-7 ]
YieldReaction ConditionsOperation in experiment
84% Example - 1: Preparation of Ethyl-2-(3-cyano-4-isobutoxy phenyl)-4-methyI thiozole -5-carboxylateA mixture of 10. Og of Ethyl -2-(3-formyl-4-hydroxy phenyl)-4-methyl thiozole -5- carboxylate and 2.85 g of hydroxylamine hydrochloride were stirred for 30 minutes in 40 g of Dimethyl sulfoxide. To this reaction mixture 3.3 grams of acetyl chloride was added and stirred at 70 -80°C for 2-3 hours. Reaction mass was cooled to room temperature and to this 19 g of potassium carbonate and 19 g of isobutyl bromide was added successively. The reaction mass was stirred for 5 hours at 70-80°C. Reaction mass was diluted with 200 ml of purified water. The reaction mass was filtered and washed with purified water to give 10.0 g of Ethyl-2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole -5-carboxyltae (yield 84.0percent)
84.0% Example-1 Preparation of Ethyl-2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole-5-carboxylate A mixture of 10.0 g of Ethyl-2-(3-formyl-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate and 2.85 g of hydroxylamine hydrochloride were stirred for 30 minutes in 40 g of Dimethyl sulfoxide. To this reaction mixture 3.3 grams of acetyl chloride was added and stirred at 70-80° C. for 2-3 hours. Reaction mass was cooled to room temperature and to this 19 g of potassium carbonate and 19 g of isobutyl bromide was added successively. The reaction mass was stirred for 5 hours at 70-80° C. Reaction mass was diluted with 200 ml of purified water. The reaction mass was filtered and washed with purified water to give 10.0 g of Ethyl-2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole-5-carboxylate (yield 84.0percent)
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Technical Information

? Acyl Group Substitution ? Appel Reaction ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chugaev Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Ester Cleavage ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stetter Reaction ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
Historical Records

Related Functional Groups of
[ 161798-01-2 ]

Aryls

Chemical Structure| 161798-03-4

[ 161798-03-4 ]

Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.96

Chemical Structure| 161797-99-5

[ 161797-99-5 ]

Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.95

Chemical Structure| 161798-02-3

[ 161798-02-3 ]

Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.92

Chemical Structure| 160844-75-7

[ 160844-75-7 ]

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

Similarity: 0.89

Chemical Structure| 33763-20-1

[ 33763-20-1 ]

4-Methyl-2-phenylthiazole-5-carboxylic acid

Similarity: 0.86

Aldehydes

Chemical Structure| 161798-03-4

[ 161798-03-4 ]

Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.96

Chemical Structure| 914348-82-6

[ 914348-82-6 ]

2-(4-Methoxyphenyl)thiazole-5-carbaldehyde

Similarity: 0.75

Chemical Structure| 1011-40-1

[ 1011-40-1 ]

2-Phenylthiazole-5-carbaldehyde

Similarity: 0.67

Chemical Structure| 20949-81-9

[ 20949-81-9 ]

2-Phenylthiazole-4-carbaldehyde

Similarity: 0.64

Chemical Structure| 53174-98-4

[ 53174-98-4 ]

Thieno[2,3-b]pyridine-2-carbaldehyde

Similarity: 0.62

Alcohols

Chemical Structure| 161797-99-5

[ 161797-99-5 ]

Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.95

Chemical Structure| 161798-02-3

[ 161798-02-3 ]

Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.92

Chemical Structure| 566169-93-5

[ 566169-93-5 ]

2-(4-(Methylamino)phenyl)benzo[d]thiazol-6-ol

Similarity: 0.66

Chemical Structure| 5556-20-7

[ 5556-20-7 ]

Ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate

Similarity: 0.57

Chemical Structure| 875237-46-0

[ 875237-46-0 ]

2-Hydroxy-4-methylthiazole-5-carboxylic acid

Similarity: 0.56

Esters

Chemical Structure| 161798-03-4

[ 161798-03-4 ]

Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.96

Chemical Structure| 161797-99-5

[ 161797-99-5 ]

Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.95

Chemical Structure| 161798-02-3

[ 161798-02-3 ]

Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.92

Chemical Structure| 160844-75-7

[ 160844-75-7 ]

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

Similarity: 0.89

Chemical Structure| 172678-67-0

[ 172678-67-0 ]

Ethyl 2-phenylthiazole-5-carboxylate

Similarity: 0.80

Related Parent Nucleus of
[ 161798-01-2 ]

Thiazoles

Chemical Structure| 161798-03-4

[ 161798-03-4 ]

Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.96

Chemical Structure| 161797-99-5

[ 161797-99-5 ]

Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.95

Chemical Structure| 161798-02-3

[ 161798-02-3 ]

Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Similarity: 0.92

Chemical Structure| 160844-75-7

[ 160844-75-7 ]

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

Similarity: 0.89

Chemical Structure| 33763-20-1

[ 33763-20-1 ]

4-Methyl-2-phenylthiazole-5-carboxylic acid

Similarity: 0.86

; ;