Potassium Carbonate → 5,5-dimethyl-3-(5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

HRID 1172072Notes

Reaction equation

HRID 1172072 reaction equation
[SH-].[Na+].[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9]([CH3:12])(=O)=O)[CH2:5]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrC[C:28]1[C:29]([C:35]([F:38])([F:37])[F:36])=[N:30][N:31]([CH3:34])[C:32]=1[F:33]>CN(C)C=O.O>[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9][CH2:12][C:28]2[C:29]([C:35]([F:38])([F:37])[F:36])=[N:30][N:31]([CH3:34])[C:32]=2[F:33])[CH2:5]1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 17862889HCID 17862889, compoundHCID 23689980Sodium Formaldehyde Sulfoxylate

Product 1

HCID 178628825,5-dimethyl-3-(5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazolineYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

19.3 g of sodium hydrosulfide (purity: 70%, 344.6 mmoles) was added to a solution of 21.3 g (120.3 mmoles) of 5,5-dimethyl-3-methylsulfonyl-2-isoxazoline dissolved in 200 ml of N,N-dimethylformamide. The mixture was stirred for 1 hour. Thereto were added 16.7 g (121.0 mmoles) of anhydrous potassium carbonate and 18.6 g (120.7 mmoles) of Rongalit. The resulting mixture was stirred for 2 hours. Thereto was added, with ice-cooling, 31.4 g (120.3 mmoles) of 4-bromomethyl-5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazole. The resulting mixture was stirred at room temperature for 2 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 29.0 g (yield: 90.3%) of 5,5-dimethyl-3-(5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline as a yellow oily substance.

Workup

  1. stirringThe resulting mixture was stirred for 2 hours
  2. additionThereto was added, with ice-
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred at room temperature for 2 hours
  5. customto give rise
  6. customto a reaction
  7. customAfter confirmation of the completion of the reaction
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe resulting organic layer was washed with water
  10. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  11. distillationThe resulting solution was subjected to vacuum distillation
  12. customto remove the solvent

Sources & evidence

ORD record
ord-da28f59525bb4f5a94fca43c40ba26ed
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

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