Aniline → 3-chloro-N-phenylbenzamide

Participants

Reaction Steps

To a solution of aniline (178 mg, 1.9 mmol) in 20 mL CH2Cl2 at room temperature was added NaOH (76.2 mg, 2.9 mmol) in 6 mL water. This mixture was stirred vigorously for 5 minutes after which 3-chlorobenzoyl chloride (500 mg, 2.9 mmol) was added drop-wise while stirring over a period of 30 minutes. This reaction mixture was stirred for an additional 2 hours followed by an acid work-up and extraction with CH2Cl2 (3×20 mL). The organic layers were combined, dried over anhydrous MgSO4. The product was purified via column chromatography on silica gel and eluted with a CHCl3/MeOH/Et3N (9.8:0.1:0.1) to give white crystals in 81% yield.

Provenance & Evidence