Malononitrile → HCID 54446985, compound

Participants

Reaction Steps

A solution of 12.1 g of triethylamine, 4.0 g of malononitrile, and 20 ml of chlorobenzene was added to a slurry of 11.4 g of N-(dichloromethylene)-N,N-diethylammonium chloride and 50 ml of chlorobenzene, at ambient temperature. The reaction temperature was kept below 50° by controlling the rate of addition (time required for complete addition, 30 minutes). After addition, the reaction mixture was stirred for four hours while it returned to ambient temperature. The reaction mixture was filtered and the filtrate concentrated on the rotary evaporator to give a brownish-red liquid. Vacuum distillation gave 3.7 g of liquid 3-chloro-2-cyano-3-(diethylamino)propenenitrile; b.p. 127°-131°/0.05 mm Hg. The ir and nmr spectra were consistent with the assigned structure.

Provenance & Evidence