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

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Reaction Steps

Oxalyl chloride (0.11 ml) was added dropwise to a stirred suspension of 3-dimethylaminobenzoic acid (0.18 g) in methylene chloride (10 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 solid. The solid was dissolved in methylene chloride (15 ml) and added dropwise over 5 minutes to a stirred mixture of N-(5-amino-2-chlorophenyl)-3,4-dimethoxybenzamide (0.306 g), triethylamine (0.4 ml), 4-dimethylaminopyridine (0.005 g) and methylene chloride (5 ml). The resultant mixture was stirred at 20° C. for 18 hours. The reaction mixture was washed with water and with a saturated, aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.109 g), m.p. 98-99° C.;

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