Dimethyl Sulfoxide → 3-(Pyridine-3-sulfonyl)thiophene-2-carbaldehyde

HRID 1944434Notes

Reaction equation

HRID 1944434 reaction equation
Cl[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[Na+].[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([O-:18])=[O:17])[CH:11]=1.CS(C)=O>O>[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([C:2]2[CH:6]=[CH:5][S:4][C:3]=2[CH:7]=[O:8])(=[O:18])=[O:17])[CH:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 27358253-Chlorothiophene-2-carbaldehydeHCID 23697071Sodium pyridine-3-sulfinate

Product 1

HCID 866521933-(Pyridine-3-sulfonyl)thiophene-2-carbaldehydeYield 28.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-chlorothiophene-2-carbaldehyde (0.16 g), pyridine-3-sulfinic acid sodium salt (0.30 g) and dimethyl sulfoxide (2.0 mL) was heated at 80° C. for 3 hours and then at 90° C. for 3 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined organic extract was dried over magnesium sulfate. The solvent was removed under reduced pressure to afford the title compound as a grey solid (0.079 g).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe combined organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0017927d9ad14a2eb52085da64a7ee85
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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