反应详情

To a solution of boron trichloride (55 g) in 1,2-dichloroethane (200 ml) at 0° was added dropwise a solution of aniline (39.1 g, 0.42 mol) in 1,2-dichlorolethane (50 ml) maintaining the temperature below 5°. On completion of the addition 4-chlorobutyronitrile (41.4 g, 0.42 mol) and aluminium chloride (53.34 g, 0.42 mol) were added successively and the reaction mixture allowed to warm up to room temperature then heated under reflux for 20 hours. After allowing to cool, 2N hydrochloric acid (100 ml) was added and the reaction mixture heated under reflux for 0.5 hour. The solid obtained was collected by filtration, taken up in water and extracted with chloroform (5×200 ml). The chloroform extracts were combined, washed with dilute base, then water, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was dissolved in ether and ethanolic HCl was added, the resulting solid was collected by filtration and dried, 28.5 g. Recrystallization from ethanol/diethyl ether gave the product, m.p. 152-154°

1. temperaturemaintaining the temperature below 5°
2. additionwere added successively
3. temperaturethen heated
4. temperatureunder reflux for 20 hours
5. temperatureto cool
6. temperaturethe reaction mixture heated
7. temperatureunder reflux for 0.5 hour
8. customThe solid obtained
9. filtrationwas collected by filtration
10. extractionextracted with chloroform (5×200 ml)
11. washwashed
12. additionwith dilute base
13. dry with materialwater, dried over magnesium sulphate
14. filtrationfiltered
15. customevaporated under reduced pressure
16. customto give an oil
17. filtrationthe resulting solid was collected by filtration
18. customdried
19. customRecrystallization from ethanol/diethyl ether
20. customgave the product, m.p. 152-154°