m-Chloroperbenzoic acid → HCID 86644423, compound

HRID 2404503Notes

Reaction equation

HRID 2404503 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([O:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])[CH:6]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16]([CH2:17][C:18]([F:20])([F:21])[F:19])=[O:41])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([O:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:29])([F:30])[F:28])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644422HCID 86644422, compound

Product 1

HCID 86644423HCID 86644423, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.2 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole was dissolved in 10 mL of chloroform, and 0.1g of m-chloroperbenzoic acid (purity: 75%) was added under cooling with ice. After stirring for 30 minutes under cooling with ice, the solution was washed with an aqueous sodium thiosulfate solution and then washed with an aqueous potassium carbonate solution, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:2) to obtain 0.2 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. washthe solution was washed with an aqueous sodium thiosulfate solution
  4. washwashed with an aqueous potassium carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-4aa1a37cae6141b1b74087762248a1fc
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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