Dimethylformamide → Ethyl 2-(1H-indol-2-yl)thio-2-phenylpropionate

HRID 846668ノート

反応式

HRID 846668 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[S:10].Br[C:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].CN(C=O)C.[OH-].[Na+]>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:12]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 30323102-IndolinethioneHCID 3778911Ethyl 2-bromo-2-phenylpropanoate

生成物 1

HCID 15724966Ethyl 2-(1H-indol-2-yl)thio-2-phenylpropionate収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Into a solution of 1,3-dihydroindol-2-thione (19.7 g) and ethyl 2-bromo-2-phenylpropionate (33.9 g) indimethylformamide (DMF, 200 ml), an aqueous 2 N sodium hydroxide solution (66 ml) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, and was extracted with ethyl acetate. The organic layer was washed with water, and then with saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. n-Hexane was added to the evaporation residue to cause crystallization. The resulting crystalline matter was recrystallized from ethyl acetate/n-hexane to give 30.3 g (yield: 71%) of product compound as a pale yellow crystal form. The melting point was 97°-99° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionn-Hexane was added to the evaporation residue
  6. customcrystallization
  7. customThe resulting crystalline matter was recrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-e97b61a07a134679ae96f86d8cf9b36c
出典データセット
uspto-grants-1992_08
特許番号
US05137909

反応ノート

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