Sodium Thiosulfate → HCID 484072, compound

HRID 636857Notes

Reaction equation

HRID 636857 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:22])([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:10](SCC)([F:12])[F:11].Cl[C:24]1C=CC=C(C(OO)=O)[CH:25]=1.[S:34]([O-:38])([O-])(=[O:36])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:22])([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:10]([S:34]([CH2:24][CH3:25])(=[O:38])=[O:36])([F:12])[F:11]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10664501HCID 10664501, compound

Product 1

HCID 484072HCID 484072, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-difluorophenyl)-1-(ethylthio)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-2-propanol (850 mg, 2.39 mmol) in dichloromethane (100 ml), 85% m-chloroperbenzoic acid (1.4 g, 5.75 mmol) was added at room temperature, followed by stirring at room temperature for 12 hours. After the completion of the reaction, a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium bicarbonate were added and the resulting mixture was stirred. The dichloromethane solution was separated and after washing with water, dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue so obtained was crystallized from isopropyl ether-ethyl acetate, whereby 2-(2,4-difluorophenyl)-1-(ethylsulfonyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-2-propanol (718 mg, yield: 78%) was obtained as colorless crystals.

Workup

  1. customAfter the completion of the reaction
  2. stirringthe resulting mixture was stirred
  3. customThe dichloromethane solution was separated
  4. washafter washing with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe residue so obtained
  8. customwas crystallized from isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-77495d30c4154862ad29148b9abc1ad9
Source dataset
uspto-grants-2001_02
Patent number
US06194592B1

Reaction notes

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