m-Chloroperbenzoic acid → HCID 86644445, compound

HRID 2404519Notes

Reaction equation

HRID 2404519 reaction equation
[CH3:1][NH:2][C:3]1[N:7]([C:8]2[CH:13]=[C:12]([S:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:11]([CH3:20])=[CH:10][C:9]=2[F:21])[N:6]=[C:5]([O:22][C:23]([F:31])([F:30])[CH:24]([F:29])[C:25]([F:28])([F:27])[F:26])[CH:4]=1.ClC1C=CC=C(C(OO)=[O:40])C=1>C(Cl)(Cl)Cl>[F:21][C:9]1[CH:10]=[C:11]([CH3:20])[C:12]([S:14]([CH2:15][C:16]([F:19])([F:18])[F:17])=[O:40])=[CH:13][C:8]=1[N:7]1[C:3]([NH:2][CH3:1])=[CH:4][C:5]([O:22][C:23]([F:30])([F:31])[CH:24]([F:29])[C:25]([F:26])([F:27])[F:28])=[N:6]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644446HCID 86644446, compound

Product 1

HCID 86644445HCID 86644445, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.4 g of 5-methylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)pyrazole was dissolved in 10 mL of chloroform, and 190 mg of m-chloroperbenzoic acid (purity: 75%) was added under cooling with ice. After stirring for 1 hour under cooling with ice, the solution was washed with an aqueous sodium thiosulfate solution and then washed with an aqueous sodium hydrogen carbonate solution, and then dried over anhydrous sodium sulfate. 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 0.4 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methylaminopyrazole.

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 sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe 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-1206f08c3ae549a780f55ea79dec2c77
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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