Acetonitrile → (2Z)-3-Amino-3-[4-(trifluoromethyl)phenyl]prop-2-enenitrile

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Reaction Steps

Under argon, 28.1 g (278 mmol) of diisopropylamine were initially charged in 450 ml of THF at −70° C. in a three-necked flask with mechanical stirrer. 148 ml of N-butyllithium solution (1.6 M in hexane, 237 mmol) were added dropwise at such a rate that the temperature did not exceed −60° C. The mixture was stirred for 10 min, and a solution of 12.9 ml (245 mmol) of acetonitrile in 100 ml of THF was then slowly added dropwise and the suspension was stirred for 30 min. A solution of 28 g (164 mmol) of 4-(trifluoromethyl)benzonitrile in 100 ml of THF was added dropwise, and the mixture was stirred at −70° C. for 20 min. The mixture was allowed to slowly warm to RT and stirred at RT for a further 16 h. 150 ml of water were added, most of the THF was distilled off and water and dichloromethane were added. The organic phase was washed with saturated aqueous sodium chloride solution. Removal of the solvent gave crystals which were purified by trituration with diisopropyl ether (once with 40 ml, twice with 20 ml). The crystals were filtered off, washed with petroleum ether and dried. This gave 27 g (78% of theory) of the product as a solid.

Provenance & Evidence