反应详情

To a solution of 20 g of N-(2-chloroethyl)-N'-(3-pyridyl) urea dissolved in 200 ml of dimethyl sulfoxide, 13 g of KOH powder was added under ice-cooling, and the mixture was stirred at room temperature for 1.5 hours. Further, 3.4 g of KOH powder was added and then 16.8 g of cinnamyl chloride (trans-form) was added under ice-cooling and the mixture was stirred for 20 minutes, followed by stirring at room temperature for 30 minutes. The mixture was diluted with 300 ml of water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, saturated saline water ad dried, and ethyl acetate was distilled off. To the residue was added 100 ml of 70% acetic acid, and the mixture was heated at 90° C. for 10 minutes and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed twice with saturated saline water and twice with water, and dried. After distilling the ethyl acetate off, the residue was recrystallized from ethanol to give 21.96 g of (E)-1-cinnamyl-3-(3-pyridyl)-2-imidazolidinone.

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred for 20 minutes
4. stirringby stirring at room temperature for 30 minutes
5. extractionextracted with ethyl acetate
6. washThe ethyl acetate layer was washed with water, saturated saline water ad
7. customdried
8. distillationethyl acetate was distilled off
9. additionTo the residue was added 100 ml of 70% acetic acid
10. temperaturethe mixture was heated at 90° C. for 10 minutes
11. concentrationconcentrated under reduced pressure
12. dissolutionThe residue was dissolved in ethyl acetate
13. washwashed twice with saturated saline water and twice with water
14. customdried
15. distillationAfter distilling the ethyl acetate off, the residue
16. customwas recrystallized from ethanol