m-Chloroperbenzoic acid → HCID 22909677, compound

HRID 1379098Notes

Reaction equation

HRID 1379098 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-444d07b53ce14a2ea6eb69a628687151
Source dataset
uspto-grants-1997_09
Patent number
US05670533

Reaction notes

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