N,N-Diethyl-1,2,2-trichlorovinylamine (CAS NO.: ), with other name of Vinylamine, 1,2,2-trichloro-N,N-diethyl-, could be produced through the following synthetic routes.

A. N,N-Diethyl-2,2,2-trichloroacetamide. A 1-l. three-necked flask equipped with a stirrer and dropping funnel is charged with 73 g. (1.00 mole) of diethylamine, 500 ml. of ether, and a solution of 40 g. (1.00 mole) of sodium hydroxide in 160 ml. of water. The mixture is stirred and maintained at a temperature of -10° to -15° by a bath of Dry Ice and acetone while 200 g. (1.10 moles) of trichloroacetyl chloride is added in the course of 1 hour. The cooling bath is removed, the temperature is allowed to rise to 10°, and the organic layer is separated. The aqueous layer is extracted with two 50-ml. portions of ether. The ether extracts are combined, washed with 50 ml. of 5% hydrochloric acid, two 50-ml. portions of 5% sodium bicarbonate solution, and 50 ml. of water, and dried over magnesium sulfate. The ether is removed by distillation at atmospheric pressure. The residue is distilled through a short indented Claisen still head at reduced pressure. N,N-Diethyl-2,2,2-trichloroacetamide is collected at 77–79°/1.5 mm.; n_D25 1.4902–1.4912; weight 183–200 g. (84–92%).

B. N,N-Diethyl-1,2,2-trichlorovinylamine (CAS NO.: ). The reaction is carried out in a 500-ml. three-necked flask equipped with an efficient mechanical stirrer, a thermometer, a reflux condenser to which a drying tube containing calcium chloride is attached, and a 250-ml. dropping funnel with a pressure-equalizing tube. The flask is charged with 219 g. (2.00 moles) of N,N-diethyl-2,2,2-trichloroacetamide. A gas-inlet tube is attached to the dropping funnel, and dry nitrogen is passed through the apparatus for 5 minutes with stirring. The gas-inlet tube is removed briefly, 202 g. (2.00 moles) of tri-n-butylphosphine is placed in the dropping funnel, the gas-inlet tube is replaced, and nitrogen is passed through the apparatus in a slow stream; the slow flow of nitrogen is continued all during the reaction. The phosphine is added at such a rate that a temperature of 85–90° is reached in 30 minutes. The rate of addition is then slowed in order to maintain the temperature within this range. The total addition time is 45–55 minutes.

After all the phosphine has been added, the water bath is replaced by a heating mantle, and the reaction mixture is held at 85–95° for one additional hour and cooled to room temperature. The nitrogen-inlet tube, dropping funnel, and reflux condenser are removed, and the reaction flask is fitted with a 15 × 150-mm. Vigreux column for distillation under reduced pressure. The reaction mixture is then distilled. The pot temperature rises from 94° to 150° during the distillation, and the crude N,N-diethyl-1,2,2-trichlorovinylamine, weight 151–164 g., is collected at 73–120°/8–11 mm. Redistillation of the crude vinylamine through a 20 × 400-mm. column packed with glass helices affords 140–150 g. (69–74%) of pure N,N-diethyl-1,2,2-trichlorovinylamine, b.p. 78–79°/18 mm., n_D25 1.4857–1.4867.