Sodium Carbonate → 2-(p-Chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole

HRID 129626Notes

Reaction equation

HRID 129626 reaction equation
[F:1][C:2]([F:6])([F:5])[S:3]Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC.O.CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[NH:15][C:16]([S:3][C:2]([F:6])([F:5])[F:1])=[CH:17][CH:18]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 67900Methanesulfenyl chloride, trifluoro-HCID 2724282-(4-Chlorophenyl)-1h-pyrrole

Product 1

HCID 189304232-(p-Chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584184Diethylether waterSolvent

Procedure

Trifluoromethylsulfenyl chloride is bubbled into a solution of 2-(p-chlorophenyl)pyrrole (0.5 g, 0.00281 mol) and sodium carbonate (0.36 g, 0.00338 mol) in ether at -30° C. under nitrogen. The reaction mixture is stirred for 1/2 hour and diluted with a water/ether mixture. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a purple solid (0.78 g, mp 34°-39° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. customThe organic phase is separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5932f01af404e01bc526dd5290de688
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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