Dimethylformamide → Methyl(1-((2,4-dichlorphenoxy)acetyl)-3-methyl-2-imidazolidinylidene)nitroacetate

Participants

Reaction Steps

2.3 g of sodium hydride was slurried in 75 ml of dimethylformamide at 5°. To that slurry, at 5°, was added 19.5 g of 1B over a 30-minute period. The stirred mixture was allowed to warm to room temperature and stirred at that temperature for one hour. The mixture then was cooled to 5° and there was added thereto a solution of 25.5 g of 2,4-dichlorophenoxyacetyl chloride in 25 ml of dimethylformamide, over a 20-minute period, the stirred mixture being held at 5°-12°. The stirred mixture was allowed to warm to room temperature and stirred at that temperature overnight. The mixture then was poured into ice water. The solid was filtered, washed with water and dried by air aspiration and ether washing to give a tan-colored solid, which on recrystallization from acetonitrile gave 1, as an off-white solid, m.p.; 191°-192° (with decomposition).

Provenance & Evidence