Water → 3-(5-chloro-3-difluoromethyl-1-methyl-1H-pyrazol-4-ylmethylsulfonyl)-5,5-dimethyl-2-isoxazoline

HRID 1172080Notes

Reaction equation

HRID 1172080 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([CH:19]([F:21])[F:20])[C:14]=1[CH2:22][S:23][C:24]1[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][N:25]=1.[OH2:31]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([CH:19]([F:21])[F:20])[C:14]=1[CH2:22][S:23]([C:24]1[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][N:25]=1)(=[O:9])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 178628833-(5-chloro-3-difluoromethyl-1-methyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

Product 1

HCID 178629243-(5-chloro-3-difluoromethyl-1-methyl-1H-pyrazol-4-ylmethylsulfonyl)-5,5-dimethyl-2-isoxazolineYield 85.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.6 g of m-chloroperbenzoic acid (purity: 70%, 14.5 mmoles) was added, with ice-cooling, to a solution of 1.8 g (5.8 mmoles) of 3-(5-chloro-3-difluoromethyl-1-methyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline dissolved in 15 ml of chloroform. The mixture was stirred at room temperature for 22 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogensulfite solution, an aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The resulting crystals were washed with hexane to obtain 1.7 g (yield: 85.9%) of 3-(5-chloro-3-difluoromethyl-1-methyl-1H-pyrazol-4-ylmethylsulfonyl)-5,5-dimethyl-2-isoxazoline as white crystals (melting point: 78 to 79° C.).

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction with chloroform
  5. washThe resulting organic layer was washed with an aqueous sodium hydrogensulfite solution
  6. dry with materialan aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. washThe resulting crystals were washed with hexane

Sources & evidence

ORD record
ord-67317f103dc848f39039f3687d6ab8da
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

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