Triethylamine → 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)benzamide

Participants

Reaction Steps

To a well-stirred mixture of 0.62 g (3.3 mmol) of 3-amino-1-chloro-3-methyl-2-pentanone hydrochloride and 25 mL of methylene chloride in a 50 mL round-bottomed flask, placed in an ice bath, was added dropwise 0.91 g (9 mmol) triethylamine. After 15 minutes 0.44 g (3 mmol) 3,5-dichlorobenzoyl chloride in methylene chloride (approximately 5 mL) was added dropwise. The mixture was stirred while the temperature was maintained between 0° C. to 5° C. for 1 hour. The reaction mixture was warmed to room temperature and stirred for 3 hours. The reaction mixture was then poured into a mixture of ethyl acetate and water. The mixture separated into phases, an organic and an aqueous phase. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate (1×50 mL), water (1×50 mL), 2.5% aqueous hydrochloric acid (1×50 mL), and water (1×50 mL). The organic layer was dried over anhydrous magnesium sulfate, treated with charcoal and filtered through Celite™ and the solvent was removed in a rotary evaporator yielding 0.6 g of 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)benzamide as a white solid (mp 159°-161° C.).

Provenance & Evidence