Sodium Thiosulfate → 1-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)sulfonyl]propyl}-1H-1,2,4-triazole

HRID 613399Notes

Reaction equation

HRID 613399 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:24][CH3:25])([C:16]([F:23])([F:22])SCCOC)[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.ClC1C=CC=[C:29]([C:33]([O:35]O)=O)C=1.[S:37]([O-:41])([O-])(=[O:39])=S.[Na+].[Na+].[C:44](=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]([O:24][CH3:25])([C:16]([F:23])([F:22])[S:37]([CH2:29][CH2:33][O:35][CH3:44])(=[O:41])=[O:39])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 154334171-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)thio]propyl}-1H-1,2,4-triazole

Product 1

HCID 99534251-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)sulfonyl]propyl}-1H-1,2,4-triazoleYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)thio]propyl}-1H-1,2,4-triazole (800 mg, 2.12 mmol) in dichloromethane (10 ml), 85% m-chloroperbenzoic acid (1.25 g, 5.09 mmol) was added at room temperature, followed by stirring at room temperature for 3 hours. After the completion of the reaction, a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium bicarbonate were added to the reaction mixture and the resulting mixture was stirred. The dichloromethane solution was separated, washed with water, dried over magnesium sulfate and distilled off under reduced pressure. The residue so obtained was subjected to a silica gel column. From the chloroform elute fraction, 700 mg (yield: 81%) of 1-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)sulfonyl]propyl}-1H-1,2,4-triazole were obtained as a yellow oil.

Workup

  1. customAfter the completion of the reaction
  2. stirringthe resulting mixture was stirred
  3. customThe dichloromethane solution was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe residue so obtained
  8. washFrom the chloroform elute fraction

Sources & evidence

ORD record
ord-07b0b89c2e294ab4b056c98eb78f01c2
Source dataset
uspto-grants-1999_12
Patent number
US06008239

Reaction notes

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