Trimethylamine → HCID 69017197, compound

Participants

Reaction Steps

To a suspension of 5-chloro-2-methylbenzoic acid (10 g, 58.6 mmol) dichloromethane (100 ml), cooled in an ice bath, was added a solution of oxalyl chloride in dichloromethane (2 M, 33 ml, 66 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 2 hours, dimethylamine hydrochloride (9.5 g, 116 mmol) was added followed by a solution of trimethylamine (25 ml, 180 mmol) in dichloromethane (100 ml) slowly. After stirring for 3 hours, the mixture was concentrated under reduced pressure and partitioned between ethyl acetate (200 ml) and hydrochloric acid (1 M, 200 ml). The organic layer was concentrated under reduced pressure to afford 2-chloro-5, N,N,-trimethyl benzamide (11.6 g, 100% yield).

Provenance & Evidence