Potassium Carbonate → HCID 86652194, compound

HRID 1944437Notes

Reaction equation

HRID 1944437 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[CH:19]=[CH:18][S:17][C:16]=1[CH:20]=[O:21]>CS(C)=O>[N:5]1[CH:6]=[CH:7][C:2]([S:1][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[CH:20]=[O:21])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27358253-Chlorothiophene-2-carbaldehydeHCID 178418431pyridine-4-thiol

Product 1

HCID 86652194HCID 86652194, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-mercaptopyridine (1.0 g), potassium carbonate (3.7 g) and dimethyl sulfoxide (10 mL) at 0° C. was treated with 3-chlorothiophene-2-carbaldehyde (1.3 g), and the resulting mixture was stirred at room temperature for 20 hours. The mixture was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and petroleum ether (1:9 to 3:2 by volume) to afford the title compound as yellow oil (1.3 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate and petroleum ether (1:9 to 3:2 by volume)

Sources & evidence

ORD record
ord-0af6f3baa9f94c578f367f6f84acb777
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

Loading…