Methanesulfenyl chloride, trifluoro- → HCID 15572245, compound

HRID 2286589Notes

Reaction equation

HRID 2286589 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11](C(O)=O)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[F:25][C:26]([F:30])([F:29])[S:27]Cl>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([S:27][C:26]([F:30])([F:29])[F:25])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 67900Methanesulfenyl chloride, trifluoro-2×HCID 15572343HCID 15572343, compound

Product 1

HCID 15572245HCID 15572245, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.3 g (1 m mole) of 4,5-bis(4-methoxyphenyl)pyrrole-2-carboxylic acid in 5 ml ether/5 ml THF at -78° was added as a gas 0.3 g of trifluoromethanesulfenyl chloride. After 15 minutes, TLC showed no evidence of reaction, so a large excess of trifluoromethanesulfenyl chloride was added and the mixture was allowed to warm slowly to room temperature overnight, with a dry ice condenser attached for the first few hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on 100 g Silic AR CC-7 to give after recrystallization from hexane 0.15 g (40%) of 4,5-bis(4-methoxyphenyl)-2-(trifluoromethylthio)pyrrole, identical to material obtained by Method A.

Workup

  1. customno evidence of reaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by chromatography on 100 g Silic AR CC-7
  4. customto give
  5. customafter recrystallization from hexane 0.15 g (40%) of 4,5-bis(4-methoxyphenyl)-2-(trifluoromethylthio)pyrrole

Sources & evidence

ORD record
ord-1a9fa5b4ab234b23b8f50f199b56351b
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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