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

HRID 846668Notes

Reaction equation

HRID 846668 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e97b61a07a134679ae96f86d8cf9b36c
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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