Water → HCID 22934879, compound

HRID 254206Notes

Reaction equation

HRID 254206 reaction equation
[CH3:1][S:2][O-].[Na+].[Cl:5][CH2:6][C:7]1([CH3:26])[O:11][N:10]=[C:9]([S:12][CH2:13][C:14]2[C:15]([C:22]([F:25])([F:24])[F:23])=[N:16][N:17]([CH2:20][CH3:21])[C:18]=2F)[CH2:8]1.O.C(OCC)(=O)C>CN(C)C=O>[Cl:5][CH2:6][C:7]1([CH3:26])[O:11][N:10]=[C:9]([S:12][CH2:13][C:14]2[C:15]([C:22]([F:25])([F:24])[F:23])=[N:16][N:17]([CH2:20][CH3:21])[C:18]=2[S:2][CH3:1])[CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 22934872HCID 22934872, compoundHCID 23717576HCID 23717576, compound

Product 1

HCID 22934879HCID 22934879, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.21 g (9.0 mmoles) of sodium methyl thioalcoholate (in the form of a 15% aqueous solution) 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 room temperature overnight 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 to obtain a crude product of 5-chloromethyl-3-(1-ethyl-5-methylthio-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

Sources & evidence

ORD record
ord-af80fb8dc5f74387a818711b6532b502
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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