2-Chlorothiazole-4-carboxylicacid ethyl ester

2-Chlorothiazole-4-carboxylicacid ethyl ester - Names and Identifiers

Name	4-Thiazolecarboxylicacid, 2-chloro-, ethyl ester
Synonyms	Ethyl2-chloro-4-thiazolecarboxylate Ethyl 2-chloro-4-thiazolecarboxylate ETHYL 2-CHLOROTHIAZOLE-4-CARBOXYLATE 2-Chloro-4-(ethoxycarbonyl)-1,3-thiazole ETHYL 2-CHLORO-1,3-THIAZOLE-4-CARBOXYLATE Ethyl 2-chloro-1,3-thiazole-4-carboxylate 2-Chlorothiazole-4-carboxylicacid ethyl ester 2-chloro-4-Thiazolecarboxylic acid ethyl ester 2-Chlorothiazole-4-carboxylic acid ethyl ester 2-Chloro-thiazole-4-carboxylic acid Methyl ester 4-Thiazolecarboxylicacid, 2-chloro-, ethyl ester 4-Thiazolecarboxylic acid, 2-chloro-, ethyl ester
CAS	41731-52-6

2-Chlorothiazole-4-carboxylicacid ethyl ester - Physico-chemical Properties

Molecular Formula	C6H6ClNO2S
Molar Mass	191.64
Density	1.383
Boling Point	283.9℃
Flash Point	125.5℃
Appearance	White powder
pKa	-1.50±0.10(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C

2-Chlorothiazole-4-carboxylicacid ethyl ester - Reference Information

Preparation

Ethyl 2-chlorothiazol-4-formate can be prepared from 2-amino-thiazol-4-ethyl formate by diazotization and later chlorination, or it can be prepared by ring-closing ethyl 3-bromopyruvate and thiourea in a basic strip. The synthesis reaction formula of 2-chlorothiazol-4-ethyl formate is shown in the following figure: Figure 1 Synthesis reaction formula of 2-chlorothiazol-4-ethyl formate Method 1. place thiourea and ethyl bromide pyruvate in 100 mL of egga-shaped bottles, add 50 mL of ethanol, reflux at 78 ℃ for 4 hours, and monitor the reaction completely by thin layer chromatography. Evaporate the solvent, add water to re-dissolve, dichloromethane extraction for 3 times, merge the organic layer, wash the saturated sodium chloride aqueous solution for 3 times, dry the anhydrous sodium sulfate, filter, concentrate and evaporate the organic solvent under reduced pressure to obtain yellow oil, Diethyl ether pulping, filter out insoluble matter, evaporate the ether solution to obtain a yellow solid with a yield of 70. 7%. Methods Thiourea and N, N-dimethylformamide 60mL were 2. added to a 100 mL round bottom flask, stirred at 45 ℃ for 20 minutes, ethyl 3-bromopyruvate was added, heated to 80 ℃ for 2.5 hours, cooled to room temperature, adjusted pH to 1 with 36% concentrated hydrochloric acid, pumped and filtered to obtain yellow solid, washed with water and dried to obtain light yellow solid. The crude product was purified by column chromatography with ethyl acetate and petroleum ether as eluents to obtain a white solid, namely 2-aminothiazole-4-ethyl formate.

Last Update：2024-04-09 15:16:35