N-Methyloxindole → 1,3-Dihydro-1-methyl-2H-indole-2-thione

HRID 1086508Notes

Reaction equation

HRID 1086508 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18]>O1CCCC1>[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=[S:18]

Participants

5

Reactant 3

HCID 6096N-MethyloxindoleHCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium Bicarbonate

Product 1

HCID 261561,3-Dihydro-1-methyl-2H-indole-2-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

148 g (1.76 mol) of sodium bicarbonate are added in 20-gram portions with brisk stirring and at room temperature to a suspension of 130 g (0.8 mol) of 1-methyl-2-indolinone, prepared according to R. A. ABRAMOVITCH and D. H. HEY (J. Chem. Soc., 1954, 1699) and 133 g (0.3 mol) of phosphorus pentasulfide in 1.30 1 of anhydrous tetrahydrofuran. After 10 hours' stirring at room temperature, the mixture is filtered and the filtrate is concentrated on a water bath under vacuum. The residue is taken up with a water/ice mixture and the resulting mixture is extracted three times with chloroform. The organic phase is washed with water and then with saturated aqueous sodium chloride solution, dried and evaporated to dryness. The residue is recrystallized in methanol.

Workup

  1. customprepared
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated on a water bath under vacuum
  4. extractionthe resulting mixture is extracted three times with chloroform
  5. washThe organic phase is washed with water
  6. dry with materialwith saturated aqueous sodium chloride solution, dried
  7. customevaporated to dryness
  8. customThe residue is recrystallized in methanol

Sources & evidence

ORD record
ord-b5fb62b22cfe47e3a699846361ca4946
Source dataset
uspto-grants-1991_07
Patent number
US05030646

Reaction notes

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