Acetonitrile → 3-Amino-3-(2,4-dichlorophenyl)acrylonitrile

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Reaction Steps

90 g (889.46 mmol) of diisopropylamine are introduced into 1660 ml of THF at −70° C. in a three-necked flask with mechanical stirrer under argon. 124.66 ml of N-butyllithium solution (2.5M in hexane, 758.66 mmol) are added dropwise at a rate such that the temperature does not rise above −60° C. The mixture is stirred for 10 min and then a solution of 32.22 g (784.82 mmol) of acetonitrile in 340 ml of THF is slowly added dropwise, and the suspension is stirred for 30 min. Then a solution of 90 g (523.21 mmol) of 2,4-dichlorobenzonitrile in 340 ml of THF is added dropwise, and the mixture is stirred at −70° C. for 20 min. It is allowed slowly to reach RT and is stirred at RT for a further 16 h. 600 ml of water are added, most of the THF is distilled off, and water and dichloromethane are added. The organic phase is washed with sat. aqueous sodium chloride solution. Removal of the solvent results in dark crystals which are purified by stirring with diethyl ether. 76.5 g (69% of theory) of the product are obtained as a solid.

Provenance & Evidence