Dimethylformamide → 4-chloro-N,N-diethyl-2-(trifluoromethyl)benzamide

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Reaction Steps

To a solution of 4-chloro-2-(trifluoromethyl)benzoic acid (18.1 g, 80 mmol) in 500 mL of methylene chloride was added oxalyl chloride (60 mL of a 2.0 M solution in methylene chloride, 120 mmol) followed by N,N-dimethylformamide (0.2 mL). The reaction was allowed to stir at ambient temperature for 18 h. The volatiles were removed in vacuo to afford the crude acid chloride intermediate. The residue was taken up in 500 mL of methylene chloride and then there was added diethylamine (16.5 mL, 160 mmol). The resulting solution was allowed to stir at ambient temperature for 2 h, and then the mixture was concentrated to an oil. The residue was purified (ISCO, 0-30% EtOAc/hexane, 45 min) to afford 11.4 g (51%) of the title compound as a pale yellow oil.

Provenance & Evidence