m-Chloroperbenzoic acid → HCID 86644470, compound

HRID 2404539Notes

Reaction equation

HRID 2404539 reaction equation
[Cl:1][C:2]1[C:3]([O:23][C:24]([F:32])([F:31])[CH:25]([F:30])[C:26]([F:29])([F:28])[F:27])=[N:4][N:5]([C:9]2[CH:14]=[C:13]([S:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:12]([CH3:21])=[CH:11][C:10]=2[F:22])[C:6]=1[NH:7][CH3:8].ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:23][C:24]([F:31])([F:32])[CH:25]([F:30])[C:26]([F:27])([F:28])[F:29])=[N:4][N:5]([C:9]2[CH:14]=[C:13]([S:15]([CH2:16][C:17]([F:20])([F:19])[F:18])=[O:41])[C:12]([CH3:21])=[CH:11][C:10]=2[F:22])[C:6]=1[NH:7][CH3:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644469HCID 86644469, compound

Product 1

HCID 86644470HCID 86644470, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.24 g of 4-chloro-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methylaminopyrazole was dissolved in 10 mL of chloroform, and 120 mg of m-chloroperbenzoic acid (purity: 75%) was added under cooling with ice. After stirring for one 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. 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 0.24 g of 4-chloro-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. 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-cecdae981d094af3ba1519500504cfcf
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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