Water → HCID 22934885, compound

HRID 254205Notes

Reaction equation

HRID 254205 reaction equation
C[O-].[Na+].[Cl:4][CH2:5][C:6]1([CH3:25])[O:10][N:9]=[C:8]([S:11][CH2:12][C:13]2[C:14]([C:21]([F:24])([F:23])[F:22])=[N:15][N:16]([CH2:19][CH3:20])[C:17]=2F)[CH2:7]1.O.[C:27](OCC)(=[O:29])C>CO>[Cl:4][CH2:5][C:6]1([CH3:25])[O:10][N:9]=[C:8]([S:11][CH2:12][C:13]2[C:14]([C:21]([F:24])([F:23])[F:22])=[N:15][N:16]([CH2:19][CH3:20])[C:17]=2[O:29][CH3:27])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 22934872HCID 22934872, compound

Product 1

HCID 22934885HCID 22934885, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4.3 g (22.5 mmoles) of sodium methoxide (in the form of a 28% methanol solution) was added, at room temperature, into a solution of 5.4 g (15.0 mmoles) of 5-chloromethyl-3-(1-ethyl-5-fluoro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline dissolved in 30 ml of methanol. The mixture was heated for refluxing for 8 hours, to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 3.3 g (yield: 59.1%) of 5-chloromethyl-3-(1-ethyl-5-methoxy-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-meth-yl-2-isoxazoline.

Workup

  1. temperatureThe mixture was heated
  2. temperaturefor refluxing for 8 hours
  3. customto give rise
  4. customto a reaction
  5. customAfter the completion of the reaction
  6. washThe resulting organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to reduced pressure distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5abb7f45d1814f23b9101a4ab7221e94
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

Loading…