Water → 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethanesulfinyl)-5,5-dimethyl-2-isoxazoline

HRID 854139Notes

Reaction equation

HRID 854139 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[CH2:14][S:15][C:16]1[CH2:20][C:19]([CH3:22])([CH3:21])[O:18][N:17]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.O>C(Cl)(Cl)Cl>[F:23][CH:2]([F:1])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:12])([F:13])[F:11])[C:5]=1[CH2:14][S:15]([C:16]1[CH2:20][C:19]([CH3:21])([CH3:22])[O:18][N:17]=1)=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 116174263-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

Product 1

HCID 230756793-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethanesulfinyl)-5,5-dimethyl-2-isoxazolineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6.2 g (17.3 mmol) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline in 40 ml of chloroform was added 3.4 g (purity: 70%, 13.8 mmol) of m-chloroperbenzoic acid under ice-cooling, followed by 1 hour of stirring. Thereafter, the whole was further stirred at room temperature for 3 hours. After the completion of the reaction was confirmed, the reaction solution was poured into water and extracted with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogen sulfite solution, an aqueous sodium hydrogen carbonate, water, and saline, successively, and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting solid was washed with n-hexane to obtain 4.1 g (yield: 63.2%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethanesulfinyl)-5,5-dimethyl-2-isoxazoline as a white powder (melting point: 112 to 114° C.).

Workup

  1. temperaturecooling
  2. stirringThereafter, the whole was further stirred at room temperature for 3 hours
  3. extractionextracted with chloroform
  4. washThe resulting organic layer was washed with an aqueous sodium hydrogen sulfite solution
  5. dry with materialan aqueous sodium hydrogen carbonate, water, and saline, successively, and then dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure
  7. washthe resulting solid was washed with n-hexane

Sources & evidence

ORD record
ord-a36ab2505a0f463ea8c8f660834e474e
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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