m-Chloroperbenzoic acid → HCID 18930431, compound

HRID 1464676Notes

Reaction equation

HRID 1464676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:18]([F:21])([F:20])[F:19])=[CH:11][C:12]=2[S:13][C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:18]([F:21])([F:19])[F:20])=[CH:11][C:12]=2[S:13]([C:14]([F:16])([F:17])[F:15])=[O:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18930386HCID 18930386, compound

Product 1

HCID 18930431HCID 18930431, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(p-chlorophenyl)-5-(trifluoromethyl)-3-[(trifluoromethyl)thio]pyrrole (5.5 g, 15.9 mmol) in chloroform is cooled to 0° C., treated with 3-chloroperoxybenzoic acid (5.49 g, 60%, 19.1 mmol), stirred for several hours and filtered to remove solids. The solids are dissolved into ether and the organic solution is washed with water and saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. Recrystallization of the solid from ether gives the title product as a white solid (mp 198°-200° C.) which is identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. dissolutionThe solids are dissolved into ether
  4. washthe organic solution is washed with water and saturated sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a solid
  8. customRecrystallization of the solid from ether

Sources & evidence

ORD record
ord-76c71aae05574284b1b882d6bb838995
Source dataset
uspto-grants-1994_04
Patent number
US05306827

Reaction notes

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