Water → HCID 22934892, compound

HRID 254211Notes

Reaction equation

HRID 254211 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][CH2:8][C:9]1([CH3:27])[O:13][N:12]=[C:11]([S:14][CH2:15][C:16]2[C:17]([C:23]([F:26])([F:25])[F:24])=[N:18][N:19]([CH3:22])[C:20]=2[OH:21])[CH2:10]1.[CH:28](I)([CH3:30])[CH3:29].O>CN(C)C=O.C(OCC)(=O)C>[Cl:7][CH2:8][C:9]1([CH3:27])[O:13][N:12]=[C:11]([S:14][CH2:15][C:16]2[C:17]([C:23]([F:26])([F:25])[F:24])=[N:18][N:19]([CH3:22])[C:20]=2[O:21][CH:28]([CH3:30])[CH3:29])[CH2:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178481864HCID 178481864, compound

Product 1

HCID 22934892HCID 22934892, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g (3.5 mmoles) of anhydrous potassium carbonate was added, at room temperature, into a solution of 1.0 g (2.9 mmoles) of 5-chloromethyl-3-(5-hydroxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. Thereto was added, at room temperature, 0.6 g (3.5 mmoles) of isopropyl iodide. The mixture was stirred for 30 minutes 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 0.5 g (yield: 45.0%) of 5-chloromethyl-3-(1-methyl-5-isopropoxy-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline.

Workup

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

Sources & evidence

ORD record
ord-35a759a2a18c410c8c7673ad8c768952
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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