Dimethylamine → HCID 18870829, compound

Participants

Reaction Steps

A mixture of chloroacetanilide (10.0 g, 59 mmol) in dimethylamine, 40% wt in water (100 ml) was refluxed for 4 hours. The cooled reaction mixture was partitioned between dichloromethane (100 ml) and 1M NaOH aqueous solution (100 ml). The aqueous layer was extracted twice more with dichloromethane (2×100 ml), the combined organic layers were concentrated in vacuo to a volume of approximately 100 ml and washed with water (2×100 ml) in order to remove the remaining dimethylamine. The organic layer was collected, dried over sodium sulfate and the solvent evaporated in vacuo to provide 10.2 g (97% yield) of the pure dimethylaminoacetanilide. 1H NMR (CDCl3, 200 MHz) δ: 9.1 (br. s, NH, 1H), 7.6-7.0 (m, Ar, 5H) 3.1 (s, CH2, 2H), 2.4 (s CH3, 6H).

Provenance & Evidence