m-Chloroperbenzoic acid → HCID 86644468, compound

HRID 2404537Notes

Reaction equation

HRID 2404537 reaction equation
[Cl:1][C:2]1[C:3]([O:22][C:23]([F:31])([F:30])[CH:24]([F:29])[C:25]([F:28])([F:27])[F:26])=[N:4][N:5]([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])[C:6]=1[NH2:7].ClC1C=CC=C(C(OO)=[O:40])C=1>C(Cl)(Cl)Cl>[NH2:7][C:6]1[N:5]([C:8]2[CH:13]=[C:12]([S:14]([CH2:15][C:16]([F:19])([F:18])[F:17])=[O:40])[C:11]([CH3:20])=[CH:10][C:9]=2[F:21])[N:4]=[C:3]([O:22][C:23]([F:30])([F:31])[CH:24]([F:29])[C:25]([F:26])([F:27])[F:28])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644467HCID 86644467, compound

Product 1

HCID 86644468HCID 86644468, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.3 g of 4-chloro-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)-5-aminopyrazole was dissolved in 10 mL of chloroform, and 140 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 5-amino-4-chloro 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)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 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-9d5b14b8d0d047caaa9609678c8d482c
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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