Iodine → Benzenesulfonothioic acid, 4-methyl-, S-methyl ester (9CI)

HRID 1515124Notes

Reaction equation

HRID 1515124 reaction equation
[CH3:1][S:2]SC.[C:5]1([CH3:14])[CH:10]=[CH:9][C:8]([S:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[Na+].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[C:5]1([CH3:14])[CH:10]=[CH:9][C:8]([S:11](=[O:13])([S:2][CH3:1])=[O:12])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 807Iodine2×HCID 12232Dimethyl DisulfideHCID 24477Sodium ThiosulfateHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 78672Benzenesulfonothioic acid, 4-methyl-, S-methyl ester (9CI)Yield 229.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In accordance with the method described in the literature (Synthesis 2002, 343), into a solution (12 mL) of 400 mg (4.25 mmoL) of dimethyl disulfide in methylene chloride were added 2.42 g (13.6 mmoL) of sodium p-toluenesulfinate and 2.16 g (8.50 mmoL) of iodine, followed by stirring at room temperature for 1 hour. The reaction solution was diluted with methylene chloride (12 mL), and a 1 M aqueous sodium thiosulfate solution was added thereto until the iodine color disappeared. The organic layer was washed with water (10 mL), dried over anhydrous magnesium sulfate, and filtered, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1.97 g of the heading compound as a colorless powdery substance (yield 100%).

Workup

  1. washThe organic layer was washed with water (10 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ea54f82a37e04613860e5dac4cda4f2e
Source dataset
uspto-grants-2012_07
Patent number
US08222407B2

Reaction notes

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