m-Chloroperbenzoic acid → Difpas-pyrazole

HRID 1379095Notes

Reaction equation

HRID 1379095 reaction equation
[F:1][CH:2]([F:24])[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:4]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[F:24][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:15])=[O:33])=[CH:12][CH:13]=2)[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9974904HCID 9974904, compound

Product 1

HCID 132932Difpas-pyrazoleYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(difluoromethyl)-1-(4-methoxyphenyl)-5-[4-(methylthio)phenyl]pyrazole (1 g) and m-chloroperbenzoic acid (0.56 g) in dichloromethane (23 ml) was stirred at ambient temperature for 1 hour. The mixture was washed with an aqueous solution of sodium bicarbonate, dried over magnesium sulfate, and concentrated. The oily residue was crystallized from ethanol to give crystals of 3-(difluoromethyl)-1-(4-methoxyphenyl)-5-[4-(methylsulfinyl)phenyl]pyrazole (0.82 g).

Workup

  1. washThe mixture was washed with an aqueous solution of sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe oily residue was crystallized from ethanol

Sources & evidence

ORD record
ord-539a7355c75e4fccb36840648b638ebf
Source dataset
uspto-grants-1997_09
Patent number
US05670533

Reaction notes

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