ChemicalBook CAS DataBase List Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

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

10synthesis methods

Product Name:Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
CAS Number:160844-75-7
Molecular formula:C18H20N2O3S
Molecular Weight:344.43

CarboxylatePotassium carbonate (300 g, 2.17 mol) and isobutyl bromide (142.7 g, 1.041 mol) were added to a solution of ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate (100 g, 0.347 mol) in dimethylformamide (300 mL), and the reaction mixture was heated at a temperature of about 75°C for about 8 hours. After completion of the reaction, the reaction mixture was cooled to about 40°C, and water was added. 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 Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate. (Yield: 11 lg, 92.9%)

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

78-77-3 Synthesis

78-77-3
326 suppliers
$14.00/5g

161798-01-2 Synthesis

ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate

161798-01-2
355 suppliers
$6.00/250mg

160844-75-7
375 suppliers
$11.00/250mg

Yield:160844-75-7 84%

Reaction Conditions:

Stage #1:ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate with hydroxylamine hydrochloride in dimethyl sulfoxide at 40; for 0.5 h;
Stage #2: with acetyl chloride in dimethyl sulfoxide at 70 - 80;
Stage #3:Isobutyl bromide with potassium carbonate in dimethyl sulfoxide at 20 - 80;

Steps:

1
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 84.0%)

References:

MATRIX LABORATORIES LTD;VELLENKI, Siva Rama Prasad;ARABINDA, Sahu;RAAVI, Satyanarayana;NUCHU, Ravi;DANDALA, Ramesh WO2012/66561, 2012, A1 Location in patent:Page/Page column 8

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78-77-3 Synthesis

78-77-3
326 suppliers
$14.00/5g