Hydrogen Peroxide → HCID 487678, compound

HRID 611815Notes

Reaction equation

HRID 611815 reaction equation
[F:1][C:2]([F:21])(SC)[C:3]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])([OH:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.OO.[S:24]([O-:28])([O-])(=[O:26])=S.[Na+].[Na+].[CH3:31]O>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[F:21][C:2]([F:1])([S:24]([CH3:31])(=[O:28])=[O:26])[C:3]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])([OH:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 24477Sodium ThiosulfateHCID 10853188HCID 10853188, compound

Product 1

HCID 487678HCID 487678, compound

Reagents, catalysts & solvents 1

HCID 150191Sodium Tungstate DihydrateCatalyst

Procedure

To a 10 ml solution of 0.50 g (1.6 mol) of 3,3-difluoro-2-(2',4'-difluorophenyl)-3-methylthio-1-(1H-1,2,4-triazole-1-yl)-propan-2-ol [Compound (1a-1)] in methanol, 0.01 g (0.03 mmol) of sodium tungstate dihydrate was added, followed by the dropwise addition of 0.53 g (4.7 mmol) of a 30% aqueous solution of hydrogen peroxide at room temperature under stirring. The resulting mixture was stirred at room temperature for 16 hours. To the reaction mixture, a 10% aqueous solution of sodium thiosulfate was added to decompose an excess oxidizing agent. Methanol was then distilled off under reduced pressure. To the residue, chloroform was added, followed by washing successively with water and saturated saline and drying over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The crystals so precipitated were recrystallized from chloroform, whereby 8.0 g of the title Compound (1c-1) were obtained in the form of colorless crystals (yield: 74%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 16 hours
  2. distillationMethanol was then distilled off under reduced pressure
  3. additionTo the residue, chloroform was added
  4. washby washing successively with water and saturated saline
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe crystals so precipitated
  8. customwere recrystallized from chloroform

Sources & evidence

ORD record
ord-f65f08cefe2247aaab50c8f526294a96
Source dataset
uspto-grants-1999_12
Patent number
US06002028

Reaction notes

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