Aniline → 4'-Methylbenzanilide

Participants

Reaction Steps

To a 0° C. dichloromethane (300 mL) solution of 25 mL (274 mmol) of aniline was added 16 mL (123 mmol) para-toluoyl chloride over 10 min. The mixture was stirred at room temperature for 0.5 h, treated with 200 mL of ether and filtered immediately. The filtrate was washed with 1 M HCl (2×50 mL), 0.1 M NaOH (2×50 mL), and saturated aqueous ammonium chloride, dried over Na2SO4 and concentrated. Para-methylbenzanilide (17.3 g) was obtained as a tan solid and used directly.

Provenance & Evidence