m-Chloroperbenzoic acid → HCID 22909677, compound

HRID 1078642Notes

Reaction equation

HRID 1078642 reaction equation
[F:1][CH:2]([F:25])[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]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=2)[N:4]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[F:25][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:15])=[O:34])=[CH:10][CH:9]=2)[N:5]([C:16]2[CH:21]=[CH:20][C:19]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=2)[N:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22909711HCID 22909711, compound

Product 1

HCID 22909677HCID 22909677, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 3-(difluoromethyl)-1-[3,4-(methylenedioxy)phenyl]-5-[4-(methylthio)phenyl]pyrazole (2.7 g) and m-chloroperbenzoic acid (1.8 g) in dichloromethane (80 ml) was stirred at 5° C. for 4 hours. The mixture was washed with an aqueous solution of sodium bicarbonate, dried, and concentrated. The residue (2.9 g) was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (25:1). The purified product (1.3 g) was recrystallized from isopropanol to give 3-(difluoromethyl)-1-[3,4-(methylenedioxy)phenyl]-5-[4-(methylsulfinyl)phenyl]pyrazole (0.85 g).

Workup

  1. washThe mixture was washed with an aqueous solution of sodium bicarbonate
  2. customdried
  3. concentrationconcentrated
  4. customThe residue (2.9 g) was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (25:1)
  5. customThe purified product (1.3 g) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-9259a9a494a54c2fbdc0000ed8ad109c
Source dataset
uspto-grants-1996_08
Patent number
US05550147

Reaction notes

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