Water → 5-Chloro-2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole

HRID 129620Notes

Reaction equation

HRID 129620 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O.O>C(O)(=O)C.C(OCC)(=O)C>[Cl:22][C:10]1[NH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:12]([S:13]([C:16]([F:17])([F:19])[F:18])(=[O:14])=[O:15])[CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 104480682-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole

Product 1

HCID 189304155-Chloro-2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrroleYield 38.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole (1.0 g, 0.00323 mol) in acetic acid is treated with thionyl chloride (0.43 g, 0.00323 mol), stirred for 30 minutes, poured into water and decanted to obtain a residue. The residue is dissolved in ethyl acetate and the organic solution is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a dark syrup. Flash chromatography of the syrup using silica gel and a 1:5 ethyl acetate/hexanes solution gives the title product as a yellow solid (0.43 g, mp 109°-112° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. customdecanted
  2. customto obtain a residue
  3. washthe organic solution is washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a dark syrup

Sources & evidence

ORD record
ord-b0b7428e58944f1681831cf1a251418b
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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