Dimethyl Disulfide → HCID 53763509, compound

HRID 1490338Notes

Reaction equation

HRID 1490338 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][C:9](=[O:16])[CH:8]2[CH2:17][CH2:18][OH:19].[CH3:20][S:21]SC.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][C:9](=[O:16])[C:8]2([S:21][CH3:20])[CH2:17][CH2:18][OH:19]

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 54562442HCID 54562442, compound

Product 1

HCID 53763509HCID 53763509, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 ml of dimethylformamide was added 360 mg of sodium hydride, and 1.76 g of 5,6-dimethoxy-3-hydroxyethyl-1,3-dihydro-2(2H)-indolone and 706 mg of dimethyl disulfide were added thereto. To the reaction mixture was added a sodium hydrogencarbonate aqueous solution, and the solvent was evaporated. The residue was extracted three times with methylene chloride, and the organic layer was dried over sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate) to yield 1.21 g of the title compound.

Workup

  1. additionwere added
  2. customthe solvent was evaporated
  3. extractionThe residue was extracted three times with methylene chloride
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-76cc971d04144542adc8862da2aa14a8
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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