4-Chloro-3-nitroaniline → N-(4-chloro-3-nitrophenyl)-3-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a solution of 4-chloro-3-nitroaniline (1.72 g, 10.0 mmol) in 60 mL of anhydrous DCM was added crystalline DMAP (1.22 g, 10.0 mmol). The reaction mixture was stirred until all solids dissolved, then 3-trifluoromethylbenzoyl chloride (2.71 g, 13.0 mmol) was added dropwise. The reaction mixture was left to stir at ambient temperature for 6 hrs. The completion of the reaction was monitored by TLC and LC/MS. Then it was transferred into a separatory funnel and washed with water (3×100 mL), saturated NaHCO3 (2×100 mL), brine (1×100 mL), dried over anhydrous Na2SO4 and filtered through a short pad of silica gel. Solvent was removed in vacuo to give the title product as a light-brown solid (3.4 g, 100% yield).

Provenance & Evidence