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

HRID 1292764Notes

Reaction equation

HRID 1292764 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1([CH3:28])[O:9][N:8]=[C:7]([S:10][CH2:11][C:12]2[C:13]([C:24]([F:27])([F:26])[F:25])=[N:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]=2F)[CH2:6]1.O>CN(C)C=O>[CH3:4][C:5]1([CH3:28])[O:9][N:8]=[C:7]([S:10][CH2:11][C:12]2[C:13]([C:24]([F:27])([F:26])[F:25])=[N:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]=2[N:2]([CH3:3])[CH3:1])[CH2:6]1

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 962WaterHCID 178628915,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

Product 1

HCID 178628635,5-dimethyl-3-(5-dimethylamino-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazolineYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.8 g (6.7 mmoles) of a 40% aqueous dimethylamine solution was added to a solution of 0.5 g (1.3 mmoles) of 5,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred at 100° C. for 9 hours in a sealed tube. Thereto was added 3.0 g (26.6 mmoles) of a 40% aqueous dimethylamine solution, and the resulting mixture was stirred for 9 hours 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 sodium 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 0.4 g (yield: 80.6%) of 5,5-dimethyl-3-(5-dimethylamino-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline.

Workup

  1. stirringthe resulting mixture was stirred for 9 hours
  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 sodium 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-65bc4df6593f47aea15ed26ade69da17
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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