Benzenesulfinic acid, sodium salt → 4-Benzenesulfonylthiazole-5-carbaldehyde

HRID 1944481Notes

Reaction equation

HRID 1944481 reaction equation
Cl[C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH:7]=[O:8].[Na+].[C:10]1([S:16]([O-:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O>[C:10]1([S:16]([C:2]2[N:3]=[CH:4][S:5][C:6]=2[CH:7]=[O:8])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 145013174-Chloro-1,3-thiazole-5-carbaldehyde

Product 1

HCID 866522084-Benzenesulfonylthiazole-5-carbaldehydeYield 89.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chlorothiazole-5-carbaldehyde (0.15 g), benzenesulfinic acid sodium salt (0.25 g) and dimethyl sulfoxide (7.0 mL) was stirred at 100° C. for 30 minutes. The mixture was cooled to room temperature, poured onto ice/water (50 mL) and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford the title compound as a tan oil (0.23 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. additionpoured onto ice/water (50 mL)
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2a6ec8581a2b4a66bf1d7500efc21129
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

Loading…