Tert-Butylamine → N-tert-butyl-3-(chloromethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

3-(Chloromethyl)benzoyl chloride (2.26 ml, 15.9 mmol) was added to a stirred solution of dichloromethane (50 mL) at −30° C. (cold-bath temperature) under argon. After 10 minutes stirring, a solution of tert-butylamine (1.66 mL, 15.9 mmol) and N-ethyl-N-isopropylpropan-2-amine (5.53 mL, 31.7 mmol) in dichloromethane (5 mL) was added dropwise. Stirring was continued while allowing the cold-bath temperature to slowly increase to −15° C. over 45 minutes. The reaction mixture was concentrated under vacuum to give the intermediate N-tert-butyl-3-(chloromethyl)benzamide as a white solid.

Provenance & Evidence