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

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.

1. customdoes not rise above −60° C
2. stirringthe suspension is stirred for 30 min
3. stirringthe mixture is stirred at −70° C. for 20 min
4. customto reach RT
5. stirringis stirred at RT for a further 16 h
6. distillationis distilled off
7. additionwater and dichloromethane are added
8. washThe organic phase is washed with sat. aqueous sodium chloride solution
9. customRemoval of the solvent
10. customresults in dark crystals which
11. customare purified
12. stirringby stirring with diethyl ether
13. custom76.5 g (69% of theory) of the product are obtained as a solid

ORD-Eintrag

ord-f1bd41f791ad4805bf0e94b997e79d38

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09051323B2