m-Chloroperbenzoic acid → HCID 86644495, compound

HRID 2404558Notes

Reaction equation

HRID 2404558 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][CH:21]=[O:22])=[CH:18][C:17]([O:23][CH2:24][C:25]([F:34])([F:33])[C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[N:16]1.ClC1C=CC=C(C(OO)=[O:43])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:14])([F:13])[F:12])=[O:43])=[CH:4][C:3]=1[N:15]1[C:19]([NH:20][CH:21]=[O:22])=[CH:18][C:17]([O:23][CH2:24][C:25]([F:34])([F:33])[C:26]([F:31])([F:32])[C:27]([F:30])([F:29])[F:28])=[N:16]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86644493HCID 86644493, compound

Product 1

HCID 86644495HCID 86644495, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.7 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-formylamino-3-(2,2,3,3,4,4,4-heptafluorobutoxy)pyrazole was dissolved in 20 mL of chloroform, and 360 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 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=1:1) to obtain 0.72 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-5-formylamino-3-(2,2,3,3,4,4,4-heptafluorobutoxy)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 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=1:1)

Sources & evidence

ORD record
ord-89e1dc9ee0a0433bb4b54642d116a7cf
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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