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

HRID 854136Notes

Reaction equation

HRID 854136 reaction equation
[CH2:1]([S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=O)=O)[CH3:2].[SH-].[Na+].C(=O)([O-])[O-].[K+].[K+].BrCC1[C:24]([C:33]([F:36])([F:35])[F:34])=[N:25][N:26]([CH3:32])[C:27]=1[O:28][CH:29]([F:31])[F:30]>CN(C)C=O.O>[F:31][CH:29]([F:30])[O:28][C:27]1[N:26]([CH3:32])[N:25]=[C:24]([C:33]([F:34])([F:35])[F:36])[C:2]=1[CH2:1][S:3][C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 117228384-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazoleHCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazoline

Product 1

HCID 116174263-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazolineYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.7 g (35.0 mmol) of 3-ethanesulfonyl-5,5-dimethyl-2-isoxazoline in 50 ml of N,N-dimethylformamide was added 5.6 g (purity: 70%, 70.0 mmol) of sodium hydrosulfide, followed by 1 hour of stirring at room temperature. Thereafter, 4.8 g (35.0 mmol) of potassium carbonate and 10.8 g (35.0 mmol) of 4-bromomethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole were added thereto, followed by stirring at room temperature overnight. After the completion of the reaction was confirmed, the reaction solution was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with water and saline 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 7.3 g (yield: 57.9%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as white crystals (melting point: 39 to 40° C.).

Workup

  1. stirringby stirring at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e4b32ddd01954ddb871abe5de2bf8a8e
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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