Water → 5,5-dimethyl-3-(5-ethylthio-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

HRID 1292763Notes

Reaction equation

HRID 1292763 reaction equation
[OH-].[Na+].O.[CH2:4]([SH:6])[CH3:5].[CH3:7][C:8]1([CH3:31])[O:12][N:11]=[C:10]([S:13][CH2:14][C:15]2[C:16]([C:27]([F:30])([F:29])[F:28])=[N:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:19]=2F)[CH2:9]1>CN(C)C=O>[CH3:7][C:8]1([CH3:31])[O:12][N:11]=[C:10]([S:13][CH2:14][C:15]2[C:16]([C:27]([F:30])([F:29])[F:28])=[N:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:19]=2[S:6][CH2:4][CH3:5])[CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 6343EthanethiolHCID 14798Sodium HydroxideHCID 178628915,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

Product 1

HCID 178628935,5-dimethyl-3-(5-ethylthio-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazolineYield 103.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.2 g (4.0 mmoles) of sodium hydroxide and 1 ml of water were added to a solution of 0.25 g (4.0 mmoles) of ethanethiol dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 30 minutes. Thereto was added a solution of 0.5 g (1.4 mmoles) of 5,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline dissolved in 5 ml of N,N-dimethylformamide. The resulting mixture was stirred for 1 hour to give rise to a reaction. After 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 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 0.6 g (yield: 100%) of 5,5-dimethyl-3-(5-ethylthio-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to vacuum distillation
  9. customto remove the solvent

Sources & evidence

ORD record
ord-044a275280c4470194003db9392647bc
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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