Dimethyl Sulfoxide → Ethanone, 1-(1-methyl-2-phenyl-1H-indol-3-yl)-

HRID 1194345Notes

Reaction equation

HRID 1194345 reaction equation
CS(C)=O.[C:5](=O)([O-])[O-].[K+].[K+].[C:11]1([C:17]2[NH:18][C:19]3[C:24]([C:25]=2[C:26](=[O:28])[CH3:27])=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.IC>O>[CH3:5][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]([C:26](=[O:28])[CH3:27])=[C:17]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6133641-(2-phenyl-1H-indol-3-yl)ethanone

Product 1

HCID 12311893Ethanone, 1-(1-methyl-2-phenyl-1H-indol-3-yl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylsulphoxide (12 ml) and potassium carbonate (3.31 g) were stirred for 10 min. and then 1-(2-phenyl-1H-indol-3-yl)-1-ethanone (1.41 g) was added and stirring was continued for a further 40 min. Iodomethane (0.75 ml) was added and the mixture was stirred for 2.75 h. Water (30 ml) was added and the mixture was extracted with ether (3×40 ml). The combined organic extracts were washed with water (4×40 ml), dried, and evaporated to leave an oil which was crystallised from cyclohexane to give the title compound (1.27 g), m.p. 76°-77°.

Workup

  1. stirringthe mixture was stirred for 2.75 h
  2. extractionthe mixture was extracted with ether (3×40 ml)
  3. washThe combined organic extracts were washed with water (4×40 ml)
  4. customdried
  5. customevaporated
  6. customto leave an oil which
  7. customwas crystallised from cyclohexane

Sources & evidence

ORD record
ord-f294f274d8834b7d9c82a5db6a826078
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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