Potassium Hydroxide → 2-Imidazolidinone, 1-(3-phenyl-2-propenyl)-3-(3-pyridinyl)-, (E)-

HRID 476996Notes

Reaction equation

HRID 476996 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:6].[OH-].[K+].[CH2:16](Cl)[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CS(C)=O.O>[CH2:16]([N:4]1[CH2:3][CH2:2][N:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:5]1=[O:6])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 94242Benzene, (3-chloro-1-propenyl)-HCID 256330N-(2-Chloroethyl)-N'-(3-pyridinyl)urea

Product 1

HCID 64507052-Imidazolidinone, 1-(3-phenyl-2-propenyl)-3-(3-pyridinyl)-, (E)-Yield 78.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cbc931dbd18243bcb6736b6253803cfe
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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