Ethyl thiazole-4-carboxylate

Chemical Properties

Uses

Synthesis Reference(s)

Synthesis

3973-08-8

64-17-5

14527-43-6

The general procedure for the synthesis of ethyl 4-thiazolecarboxylate from thiazole-4-carboxylic acid and ethanol was as follows: 2.5 mmol of thiazole-4-carboxylic acid and 2.0 mmol of ethanol were dissolved in 25 mL of dry dichloromethane (DCM) in a dry flask with continuous stirring. Subsequently, 2.5 mmol of 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (EDC-HCl) was added. After the temperature of the reaction system was lowered to 0 °C, 0.2 mmol of 4-dimethylaminopyridine (DMAP) was added slowly dropwise and the reaction was continued at 0 °C. After completion of the reaction, the temperature of the system was raised to room temperature and the reaction was continued with stirring for 4 hours. Upon termination of the reaction, 25 mL of saturated sodium bicarbonate (NaHCO3) solution was added and extracted twice with dichloromethane (2 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by column chromatography (eluent ratio: ethyl acetate:petroleum ether=1:5) to obtain the target compound ethyl 4-thiazolecarboxylate.

References