Dimethyl Disulfide → Methyl 4,7-dimethyl-3-methylsulfenylindole-2-carboxylate

HRID 361623Notes

Reaction equation

HRID 361623 reaction equation
CS[S:3][CH3:4].S(Cl)(Cl)(=O)=O.[CH3:10][C:11]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]2[C:12]=1[CH:13]=[C:14]([C:21]([O:23][CH3:24])=[O:22])[NH:15]2>ClCCCl.CN(C=O)C.C(OCC)(=O)C>[CH3:10][C:11]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]2[C:12]=1[C:13]([S:3][CH3:4])=[C:14]([C:21]([O:23][CH3:24])=[O:22])[NH:15]2

Participants

7

Reactant 3

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 4714976methyl 4,7-dimethyl-1H-indole-2-carboxylate

Product 1

HCID 53833292Methyl 4,7-dimethyl-3-methylsulfenylindole-2-carboxylateYield 105.1%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice-cooling, 0.89 ml (7.4 mmol) of dimethyl disulfide was dissolved in 20 ml of 1,2-dichloroethane, and 0.53 ml (6.5 mmol) of sulfuryl chloride was added. The reaction mixture was stirred for 20 minutes and a solution of 2.00 g (9.8 imnol) of methyl 4,7-dimethylindole-2-carboxylate in 10 ml of anhydrous DMF was added. The reaction mixture was stirred for 2 hours, then dissolved in ethyl acetate and washed with water. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide 1.94 g of white crystals. Yield: 80%

Workup

  1. temperatureUnder ice-cooling
  2. stirringThe reaction mixture was stirred for 2 hours
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5ecd86f17f7a45298e3846f5b76a82a7
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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