Phosgene → HCID 86612880, compound

Participants

Reaction Steps

A solution of rac-4-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-3-ethoxy-benzonitrile (190 mg, 0.31 mmol) in dichloromethane was cooled to 0° C. and treated with phosgene (2.5 mL, 0.47 mmol, 1.9 M in toluene) and triethylamine (0.66 g, 0.65 mmol). After 1 h, the reaction was charged with the same quantities of phosgene and triethylamine. After an additional 1 h at 0° C., the reaction was worked up in ice water and dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give an oil. It was purified by a short plug of silica gel (eluting with 20% ethyl acetate/hexane) to give rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(4-cyano-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride.

Provenance & Evidence