Methyl iodide → 3-(Benzenesulfinyl)-1-methyl-1H-indole

HRID 1906934Notes

Reaction equation

HRID 1906934 reaction equation
[H-].[Na+].[C:3]1([S:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:20]I>CN(C)C=O.O>[CH3:20][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:10])=[CH:12]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 134429343-(Benzenesulfinyl)-1H-indole

Product 1

HCID 138001663-(Benzenesulfinyl)-1-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride in mineral oil (60% suspension, 0.036 g, 0.90 mmol) was suspended in dry dimethylformamide (10 ml) and a solution of 3-phenylsulfinylindole (0.200 g, 0.82 mmol) in dry dimethylformamide (10 ml) was added dropwise thereto with stirring. After 0.5 hours at room temperature, methyl iodide (0.057 ml) was added and fifteen minutes thereafter the mixture was diluted with water. The product was extracted into benzene, the extract dried and evaporated in vacuo. Crystallization of the residue from ethyl acetate-ether gave the title compound as a solid.

Workup

  1. extractionThe product was extracted into benzene
  2. customthe extract dried
  3. customevaporated in vacuo
  4. customCrystallization of the residue from ethyl acetate-ether

Sources & evidence

ORD record
ord-f68d0972c06843cf8524d23e160ee5b3
Source dataset
uspto-grants-1987_03
Patent number
US04654360

Reaction notes

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