Thiophene → (2-Chloropyridin-3-yl)(thiophen-2-yl)methanone

HRID 1359305Notes

Reaction equation

HRID 1359305 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[S:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1>C(=S)=S>[Cl:1][C:2]1[C:3]([C:4]([C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15135620(2-Chloropyridin-3-yl)(thiophen-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

10 g of 2-chloronicotinic acid chloride was added to a mixture of 7.2 g of aluminum chloride and 100 ml of carbon disulfide under ice-cooling, followed by adding 8.8 ml of thiophene was slowly added dropwise thereinto. After stirring at room temperature for two nights, the reaction solution was slowly poured into ice water. The mixture was extracted with ethyl acetate, and the organic phase was successively washed with aqueous saturated sodium bicarbonate and brine. After removing the solvent, the residue was subjected to silica gel column chromatography and eluted with hexane/ethyl acetate (3:1) and then with hexane/ethyl acetate (2:1), to give 1.64 g of the target compound.

Workup

  1. temperaturecooling
  2. additionwas slowly added dropwise
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was successively washed with aqueous saturated sodium bicarbonate and brine
  5. customAfter removing the solvent
  6. washeluted with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-d90206c891a04c73911817af45175f12
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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