m-Chloroperbenzoic acid → HCID 86644451, compound

HRID 2404523Notes

Reaction equation

HRID 2404523 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N:15]1[C:19]([NH:20][CH2:21][C:22]#[CH:23])=[CH:18][C:17]([O:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[N:16]1.ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([CH2:10][C:11]([F:12])([F:13])[F:14])=[O:41])=[CH:4][C:3]=1[N:15]1[C:19]([NH:20][CH2:21][C:22]#[CH:23])=[CH:18][C:17]([O:24][CH2:25][C:26]([F:31])([F:32])[C:27]([F:28])([F:29])[F:30])=[N:16]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644450HCID 86644450, compound

Product 1

HCID 86644451HCID 86644451, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.51 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)-5-(2-propynylamino)pyrazole was dissolved in 10 mL of chloroform, and 240 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 0.39 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)-5-(2-propynylamino)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. 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-6c78f9862da94a2c9bd7016422793844
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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