Triethylamine → 4-chloro-N-methoxy-N-methylbutyramide

Participants

Reaction Steps

While under argon, a solution of N,O-dimethylhydroxylamine hydrochloride (16.9 g, 0.173 mol) and triethylamine (53 mL, 0.381 mol) in dichloromethane (240 mL) was carefully treated with 4-chlorobutyryl chloride (20 g, 0.19 mol) over 40 minutes. After the addition was complete, the reaction mixture was stirred overnight at room temperature. The solid triethylamine hydrochloride was removed by filtration and the remaining solution was washed successively with aq 2 N HCl (×2), 1M K2CO3 and saturated aqueous sodium chloride. The organic layer was dried over MgSO4, filtered and concentrated to give 4-chloro-N-methoxy-N-methylbutanamide (21.8 g) of crude yellow oil that was used in the next step without further purification. ESI MS found for C6H12ClNO2 m/z [166.0/168.0 (M+1)].

Provenance & Evidence