Water → HCID 22934878, compound

HRID 254207Notes

Reaction equation

HRID 254207 reaction equation
[C-:1]#[N:2].[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(OCC)(=O)C>CN(C)C=O>[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[C:1]#[N:2])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22934872HCID 22934872, compound

Product 1

HCID 22934878HCID 22934878, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.30 g (6.0 mmoles) of sodium cyanide was added, at room temperature, into a solution of 1.08 g (3.0 mmoles) of 5-chloromethyl-3-(1-ethyl-5-fluoro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred at 50° C. for 10 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 1.10 g (yield: quantitative) of 5-chloromethyl-3-(5-cyano-1-ethyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline.

Workup

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

Sources & evidence

ORD record
ord-4f924d7ee92f41dca8f8acc4bca9955d
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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