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

HRID 854137Notes

Reaction equation

HRID 854137 reaction equation
Br.[F:2][CH:3]([F:20])[O:4][C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:6]=1[CH2:15][S:16][C:17](=N)[NH2:18].[OH-].[Na+].O.ClC1[CH2:29][C:28]([CH3:31])([CH3:30])[O:27]N=1>C(O)C>[F:2][CH:3]([F:20])[O:4][C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:6]=1[CH2:15][S:16][C:17]1[CH2:29][C:28]([CH3:31])([CH3:30])[O:27][N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 116654173-Chloro-5,5-dimethyl-4,5-dihydro-1,2-oxazoleHCID 230756895-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl-carbamimidothioic acid methyl ester hydrobromide

Product 1

HCID 116174263-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazolineYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.93 g (5.00 mmol) of 2-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethyl)-isothiourea hydrobromide in 10 ml of ethanol were added 0.48 g (12.00 mmol) of sodium hydroxide and 10 ml of -water, followed by 30 minutes of stirring at room temperature. Thereto was added 0.67 g (5.00 mmol) of 3-chloro-5,5-dimethyl-2-isoxazoline at room temperature, followed by further 12 hours of stirring under refluxing. After the completion of the reaction was confirmed, the solvent was removed by evaporation under reduced pressure. The obtained residue was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel column chromatography to obtain 1.02 g (yield: 56.7%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline.

Workup

  1. waitfollowed by further 12 hours
  2. stirringof stirring
  3. temperatureunder refluxing
  4. customthe solvent was removed by evaporation under reduced pressure
  5. additionThe obtained residue was poured into water
  6. extractionextracted with ethyl acetate
  7. washThe resulting organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by evaporation under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1cc0cd987eda45dfb646996f7ceb8b04
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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