Hydrogen Peroxide → HCID 18969590, compound

HRID 399028Notes

Reaction equation

HRID 399028 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]([F:24])([F:23])[F:22])=[CH:11][C:12]=2[S:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[OH:25]O.O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([C:21]([F:23])([F:22])[F:24])=[CH:11][C:12]=2[S:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:25])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 10960055HCID 10960055, compound

Product 1

HCID 18969590HCID 18969590, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(p-chlorophenyl)-3-[(p-chlorophenyl)thio]-5-(trifluoromethyl)pyrrole (2.57 g, 6.6 mmol) and 30% hydrogen peroxide solution (0.83 g, 7.3 mmol) in acetic acid is stirred at room temperature overnight and poured into water. The resultant aqueous mixture is filtered to obtain a solid. A solution of the solid in methylene chloride is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and a 1:3 ethyl acetate/hexanes solution gives the title product as a white solid (1.75 g, mp 174°-176° C.)

Workup

  1. filtrationThe resultant aqueous mixture is filtered
  2. customto obtain a solid
  3. washA solution of the solid in methylene chloride is washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-2528ffec5dc740c7a19581aab5882ddb
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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