Dimethylformamide → N~2~-(2,6-Dimethylphenyl)glycinamide

Participants

Reaction Steps

Add 200 ml dimethylformamide to a mixture of 2,6-dimethylaniline (36.3 g, 0.30 mol), 2-chloroacetamide (74.8 g, 0.80 mol) and potassium carbonate (41.4 g, 0.3 mol). Heat at 120° for 72 hours, allow to cool, and pour into water. Extract with 1:1 ether-ethyl acetate. Wash the organic with 1.0 N HCl. Neutralize the aqueous layer with NaHCO3 and extract it with ethyl acetate. Dry, concentrate, and distill to collect a fraction, b.p. 157°-167°/0.1 mm. Recrystallize from methylene chloride-hexane to give as a solid, m.p. 91°-92°, N-aminocarbonylmethyl-2,6-dimethylaniline.

Provenance & Evidence