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

Under argon, 90 g (889.46 mmol) of diisopropylamine were initially charged in 1660 ml of THF at −70° C. in a three-necked flask with mechanical stirrer. 124.66 ml of N-butyllithium solution (2.5 M in hexane, 758.66 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 32.22 g (784.82 mmol) of acetonitrile in 340 ml of THF was then slowly added dropwise and the suspension was stirred for 30 min. A solution of 90 g (523.21 mmol) of 2,4-dichlorobenzonitrile in 340 ml of THF was then 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. 600 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 diethyl ether. This gave 76.5 g (69% of theory) of the product as a solid.

1. customdid not exceed −60° C
2. stirringthe suspension was stirred for 30 min
3. stirringthe mixture was stirred at −70° C. for 20 min
4. stirringstirred at RT for a further 16 h
5. distillationwas distilled off
6. additionwater and dichloromethane were added
7. washThe organic phase was washed with saturated aqueous sodium chloride solution
8. customRemoval of the solvent
9. customgave crystals which
10. customwere purified by trituration with diethyl ether

ORDレコード

ord-cebb1e0ed83a4ba4b6d18e0e701c5e20

出典データセット

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08436003B2