Pyridine → 2,5-Bis[(trifluoromethyl)sulfanyl]-1H-pyrrole

HRID 1735642Notes

Reaction equation

HRID 1735642 reaction equation
[F:1][C:2]([F:6])([F:5])[S:3]Cl.[NH:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14]C=1>C(=O)=O.C(Cl)(Cl)Cl.[Fe]>[F:1][C:2]([F:6])([F:5])[S:3][C:8]1[NH:7][C:11]([S:3][C:2]([F:6])([F:5])[F:1])=[CH:10][CH:9]=1.[F:1][C:2]([F:6])([F:5])[S:3][C:17]1[NH:12][CH:14]=[C:15]([S:3][C:2]([F:6])([F:5])[F:1])[CH:16]=1

Participants

8

Reactant 3

HCID 1049PyridineHCID 8027PyrroleHCID 67900Methanesulfenyl chloride, trifluoro-

Product 2

HCID 125083162,5-Bis[(trifluoromethyl)sulfanyl]-1H-pyrroleHCID 125083222,4-Bis[(trifluoromethyl)sulfanyl]-1H-pyrrole

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 280Carbon DioxideSolventHCID 6212ChloroformSolvent

Procedure

25 g of trifluoromethanesulfenyl chloride was condensed in a pressured bottle in dry ice and 2.34 g of pyrrole in 40 ml of anhydrous chloroform, 12.1 g of pyridine and 0.8 g of iron powder were added. The mixture was then stirred at room temperature for 3 days. It was then filtered to remove insoluble materials. The mixture was washed with water, diluted hydrochloric acid and water again. After evaporation of the solvent, the residue was distilled under vacuum, giving 4.2 g of 2,5-bis(trifluoromethylthio)pyrrole and 3.5 g 2,4-bis(trifluoromethylthio)pyrrole. The total yield was 82%.

Workup

  1. filtrationIt was then filtered
  2. customto remove insoluble materials
  3. washThe mixture was washed with water, diluted hydrochloric acid and water again
  4. customAfter evaporation of the solvent
  5. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-97155b9936e34cadbc7e11a8c90454f4
Source dataset
uspto-grants-1996_07
Patent number
US05538812

Reaction notes

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