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

HRID 1172074Notes

Reaction equation

HRID 1172074 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[CH3:11][C:12]1([CH3:30])[O:16][N:15]=[C:14]([S:17][CH2:18][C:19]2[C:20]([C:26]([F:29])([F:28])[F:27])=[N:21][N:22]([CH3:25])[C:23]=2F)[CH2:13]1.O>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:23]1[N:22]([CH3:25])[N:21]=[C:20]([C:26]([F:28])([F:27])[F:29])[C:19]=1[CH2:18][S:17][C:14]1[CH2:13][C:12]([CH3:30])([CH3:11])[O:16][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72452-ChlorophenolHCID 24758Sodium hydrideHCID 178628825,5-dimethyl-3-(5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

Product 1

HCID 178628543-(5-(2-chlorophenoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazolineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.2 g (8.3 mmoles) of sodium hydride (purity: 60%) was added, with ice-cooling, to a solution of 0.44 g (3.4 mmoles) of 2-chlorophenol dissolved in 30 ml of N,N-dimethylformamide. The mixture was stirred for 1 hour. Thereto was added 0.7 g (2.2 mmoles) of 5,5-dimethyl-3-(5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline. The resulting mixture was stirred at 120 to 130° C. for 5 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. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.63 g (yield: 66.7%) of 3-(5-(2-chlorophenoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as a yellow oily substance.

Workup

  1. stirringThe resulting mixture was stirred at 120 to 130° C. for 5 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter confirmation of the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to vacuum distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Sources & evidence

ORD record
ord-17ab85fdbb5141acba8768cc20b78efd
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

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