Dimethyl Sulfoxide → 4-Benzenesulfonyl-3-chloroisothiazole-5-carbaldehyde

HRID 1944492Notes

Reaction equation

HRID 1944492 reaction equation
[Cl:1][C:2]1[C:6](Cl)=[C:5]([CH:8]=[O:9])[S:4][N:3]=1.[Na+].[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(C)=O>O>[C:11]1([S:17]([C:6]2[C:2]([Cl:1])=[N:3][S:4][C:5]=2[CH:8]=[O:9])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 2723840Benzenesulfinic acid, sodium saltHCID 866522123,4-Dichloro-1,2-thiazole-5-carbaldehyde

Product 1

HCID 866522134-Benzenesulfonyl-3-chloroisothiazole-5-carbaldehydeYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-dichloroisothiazole-5-carbaldehyde (0.087 g), benzenesulfinic acid sodium salt (0.078 g) and dimethyl sulfoxide (3.0 mL) was stirred at room temperature for 3.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume) to afford the title compound as a colourless oil (0.093 g).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume)

Sources & evidence

ORD record
ord-89b98cd6cbf543338570c08db5c8462e
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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