Sodium Thiosulfate → HCID 10572016, compound

HRID 1108049Notes

Reaction equation

HRID 1108049 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:23])([CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[C:10]([F:16])([F:15])SCCO.ClC1C=CC=[C:27]([C:31](OO)=[O:32])C=1.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:23])([CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[C:10]([F:16])([F:15])[S:35]([CH2:27][CH2:31][OH:32])(=[O:39])=[O:37]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10665616HCID 10665616, compound

Product 1

HCID 10572016HCID 10572016, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2,4-difluorophenyl)-1,1-difluoro-1-(2-hydroxyethyl)thio-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (9.10 g, 0.026 mol) in dichloromethane (250 ml), 85% m-chloroperbenzoic acid (14.8 g, 0.073 mol) was added at room temperature, followed by stirring at room temperature for one hour. After the completion of the reaction, a saturated aqueous solution of sodium thiosulfate and a saturated solution of sodium bicarbonate were added to the reaction mixture and they were stirred. The dichloromethane solution was separated, washed with water, dried over anhydrous magnesium sulfate and then distilled off under reduced pressure. The residue so obtained was recrystallized from isopropyl ether--ethyl acetate, whereby 2-(2,4-difluorophenyl)-1,1-difluoro-1-(2-hydroxyethyl)sulfonyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (4.43 g, yield: 44.6%) was obtained as colorless crystals.

Workup

  1. customAfter the completion of the reaction
  2. stirringwere stirred
  3. customThe dichloromethane solution was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe residue so obtained
  8. customwas recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-a0aa4ddec0ef48d0b3be65bb488ca43c
Source dataset
uspto-grants-2000_05
Patent number
US06063945

Reaction notes

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