Phosphorus sulfide (P2S5) → 1-Methyl-5-Methoxy-2-Indolinethione

HRID 1086511Notes

Reaction equation

HRID 1086511 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[C:12](=O)[CH2:11]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20]>O1CCCC1>[CH3:17][N:13]1[C:14]2[C:10](=[CH:9][C:8]([O:7][CH3:6])=[CH:16][CH:15]=2)[CH2:11][C:12]1=[S:20]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 91021941,3-Dihydro-5-methoxy-1-methyl-2H-indol-2-one

Product 1

HCID 137767581-Methyl-5-Methoxy-2-Indolinethione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

18.5 g (0.22 mol) of sodium bicarbonate are added to a solution of 19.5 g (0.11 mol) of 5-methoxy-1-methyl-2-indolinone prepared according to A. H. BECKETT, R. W. DAISLEY and J. WALKER (Tetrahedron 1968, 24 6093) and 16.5 g (0.037 mol) of phosphorus pentasulfide in 200 ml of tetrahydrofuran. The reaction medium is heated to a temperature of 50° C. for 1 h 30 min and then filtered and concentrated on a water bath under vacuum. The residue is taken up with ice-cold water and the mixture is extracted with methylene chloride. The organic phase is washed with saturated sodium chloride solution, dried and evaporated. The residue is used in the next stage without further treatment.

Workup

  1. customprepared
  2. filtrationfiltered
  3. concentrationconcentrated on a water bath under vacuum
  4. extractionthe mixture is extracted with methylene chloride
  5. washThe organic phase is washed with saturated sodium chloride solution
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-5b94579deea04c9a84ebb9428ed474c1
Source dataset
uspto-grants-1991_07
Patent number
US05030646

Reaction notes

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