Triethylamine → N-[2-bromo-5-(3-dimethylaminobenzamido)phenyl]-3,4-dimethoxybenzamide

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.24 ml) was added dropwise to a stirred suspension of 3-dimethylaminobenzoic acid (0.36 g) in methylene chloride (15 ml) at 20° C. DMF (2 drops) was added and the reaction mixture was stirred for 4 hours. The solvent was evaporated to give a yellow solid which was dissolved in methylene chloride (20 ml) and added dropwise over 5 minutes to a stirred mixture of N-(5-amino-2-bromophenyl)-3,4-dimethoxybenzamide (0.7 g), triethylamine (0.8 ml), 4-dimethylaminopyridine (0.005 g) and methylene chloride (20 ml) which had been cooled to 5-10° C. The reaction mixture was stirred at ambient temperature for 18 hours. The organic phase was washed with a saturated sodium bicarbonate solution, dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 49:1 mixture of methylene chloride and methanol as eluent. The solid so obtained was crystallised from a mixture of ethyl acetate and methyl tert-butyl ether to give the title compound (0.564 g), m.p. 184° C.;

Provenance & Evidence