Potassium Carbonate → 3-(Thiophen-2-ylsulfanyl)thiophene-2-carbaldehyde

HRID 1944408Notes

Reaction equation

HRID 1944408 reaction equation
Cl[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[SH:20]>CN(C)C=O>[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5226742-ThiophenethiolHCID 27358253-Chlorothiophene-2-carbaldehyde

Product 1

HCID 866521863-(Thiophen-2-ylsulfanyl)thiophene-2-carbaldehydeYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chlorothiophene-2-carbaldehyde (1.0 g), potassium carbonate (2.8 g) and N,N-dimethylformamide (6.8 mL) was treated dropwise with thiophene-2-thiol (0.87 g), and the resulting mixture was stirred at room temperature for 3 hours. The mixture was poured onto water (150 mL) and extracted with diethyl ether. The combined organic extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was removed under reduced pressure to afford the title compound as a red oil (1.5 g).

Workup

  1. additionThe mixture was poured onto water (150 mL)
  2. extractionextracted with diethyl ether
  3. extractionThe combined organic extract
  4. washwas washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f69c132f935243e8b4ad23356c78f40f
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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