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

HRID 477004ノート

反応式

HRID 477004 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9c1e4b6d3fd14fcf80146d70ea0e3d09
出典データセット
uspto-grants-1989_12
特許番号
US04886817

反応ノート

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