Reacción #73682

Ecuación de reacción

ethyl 2-amino-4-phenylthiazole-5-carboxylate

pyridine

benzoyl chloride

→

title compound

Rendimiento 92.0%

Ethyl 2-Benzamido-4-phenylthiazole-5-carboxylate

Rendimiento 92.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 5% hydrochloric acid solution, water
2. 2
   Secadodried over anhydrous sodium sulfate
3. 3
   OtroRemoval of the solvent

Procedimiento

To a stirred cold mixture of ethyl 2-amino-4-phenylthiazole-5-carboxylate (1.24 g, 5.00 mmol), 4-dimethylaminopyridine (0.10 g, 16 mol %) and pyridine (4.0 mL, 10 equiv) in dichloromethane (20.0 mL) was added benzoyl chloride (0.70 g, 5.00 mmol) in dichloromethane (3 mL). The mixture was stirred at ambient temperature for 2 h, then washed with 5% hydrochloric acid solution, water, and dried over anhydrous sodium sulfate. Removal of the solvent afforded the title compound in 92% yield (1.62 g); 1H NMR (CDCl3, 300 MHz) δ 10.10 (s, 1H), 8.15 (d, J=7.2 Hz, 2H), 7.85-7.45 (m, 8H), 4.24 (q, J=5.9 Hz, 2H), 1.19 (t, J=5.9 Hz, 3H); MS (ES+) m/z 353.1 (M+1).

Fuente