Dimethylformamide → HCID 21558108, compound

Participants

Reaction Steps

A 273g (1.5 mole) portion of trichloroacetyl chloride was added over one hour to a stirred, cooled (5°C) portion of 330g (4.5 moles) of dimethylformamide. Nitrogen was passed over the solution throughout the reaction. A 152g (1.5 mole) portion of triethylamine was then added dropwise while keeping the temperature below 15°C. The mixture was stirred overnight at ambient temperature and then cooled to 5°C before 300 ml of water was added gradually. The organic products were extracted into ethyl ether, and the ethereal solution was washed with water, 10% hydrochloric acid, and with brine, dried over magnesium sulfate and concentrated. The residue was distilled under vacuum through a short-path still yielding 160g of pure N,N-dimethyl-3,3,3-trichloropyruvamide: Bp 80°-82° (0.2mm); ir(λmax, film) 5.7 (s), 6.0 (s), 9.45 (s), 11.6 (m) microns; nmr (δ , CDCl3) 3.0 and 3.05 (two singlets, 6H) ppm.

Provenance & Evidence