2-Chloro-N-(2,6-dimethylphenyl)acetamide → HCID 20512450, compound

Participants

Reaction Steps

6.3 g (0.0443 moles) of 2,6-dimethylphenyl-cyanamide [m.p.: 120°-122° C.; prepared from 1-(2',6'-dimethylphenyl)-thiourea according to the method of Rathke (Ber. 12, 773 /1879/; Beilstein's Handbuch der organischen Chemie 12 H, 368 /1929/)] are dissolved in 100 ml of dry dimethylformamide, 4.8 g (0.0048 moles) of potassium tert.-butoxide are added, and the mixture is stirred at room temperature for 0.5 hours. Thereafter 8.7 g (0.0443 moles) of N-chloroacetyl-2,6-dimethyl-aniline (m.p.: 145°-146° C.; prepared by acylating 2,6-dimethylaniline with chloroacetyl chloride) are introduced, and the resulting mixture is stirred at 100° C. for 2 hours. The mixture is cooled, poured into water, the separated crystalline product is filtered off, washed with water and dried. This crude product is dissolved in 10% isopropanolic hydrochloric acid, and the salt is precipitated with diethyl ether. 1.7 g (12.5%) of pure 1,3-bis(2',6'-dimethylphenyl)-2-imino-4-oxo-imidazolidine hydrochloride are obtained; m.p.: 219°-221° C.

Provenance & Evidence