2-Aminothiazole → HCID 1246351, compound

Participants

Reaction Steps

To a solution of (3,4-dichloro-phenyl)-acetic acid (500 mg, 2.4 mmol)in N,N-dimethylformamide (15 mL) at 25° C. was added HBTU (1.02 g, 2.7 mmol), 2-aminothiazole (360 mg, 3.6 mmol) and diisopropylethylamine (1.25 mL, 7.2 mmol). The reaction mixture was stirred for 16 h, then was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed in turn with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1 N hydrochloric acid (1×10 mL) and brine (1×10 mL), then were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 50150 hexanes/ethyl acetate) to furnish rac-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (480 mg, 70% yield) as a light yellow solid, mp 169.8-172.3° C. EI-HRMS m/e calcd for C11H8N2OSCl2 (M+) 285.9734, found 285.9734.

Provenance & Evidence