Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 2-Imidazolidinone, 1-(3-phenyl-2-propenyl)-3-(3-pyridinyl)-, (E)-

HRID 477004Notes

Reaction equation

HRID 477004 reaction equation
[CH2:1]([NH:10][C:11]([NH:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+].Cl[CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[CH2:1]([N:10]1[CH2:24][CH2:23][N:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:11]1=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydrideHCID 14834216(E)-N-cinnamyl-N'-(3-pyridyl) urea

Product 1

HCID 64507052-Imidazolidinone, 1-(3-phenyl-2-propenyl)-3-(3-pyridinyl)-, (E)-Yield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.51 g of (E)-N-cinnamyl-N'-(3-pyridyl) urea dissolved in 30 ml of dimethylformamide, 990 mg of sodium hydride (60% oily dispersion) was added under ice-cooling and the mixture was stirred for 30 minutes. To the mixture was added 2.8 g of 1-chloro-2-p-toluenesulfonyloxyethane and the mixture was stirred under ice-cooling for 6 hours. After distilling dimethylformamide off under reduced pressure, the residue was diluted with water and extracted with chloroform. The chloroform layer was washed with water, dried and then the solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol=30:1) and recrystalliezed from ethanol to give 1.65 g of (E)-1-cinnamyl-3-(3-pyridyl)-2-imidazolidinone.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 6 hours
  4. distillationAfter distilling dimethylformamide off under reduced pressure
  5. additionthe residue was diluted with water
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with water
  8. customdried
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol=30:1)

Sources & evidence

ORD record
ord-9c1e4b6d3fd14fcf80146d70ea0e3d09
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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