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

HRID 613395Notes

Reaction equation

HRID 613395 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]([OH:26])([CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)[C:12]([F:19])([F:18])[S:13][CH2:14][CH2:15][O:16][CH3:17].[CH3:27]I.O>CN(C)C=O>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]([O:26][CH3:27])([C:12]([F:18])([F:19])[S:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15433416HCID 15433416, compound

Product 1

HCID 154334171-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)thio]propyl}-1H-1,2,4-triazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 60% sodium hydride (131 mg, 3.29 mmol) in N,N-dimethylformamide (50 ml), 2-(2,4-difluorophenyl)-1,1-difluoro-1-[(2-methoxyethyl)thio]-3-(1H-1,2,4-triazol-1-yl)-2-propanol (1.0 g, 2.74 mmol) was added dropwise under ice cooling. The resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture, methyl iodide (516 mg, 3.56 mmol) was added dropwise under ice cooling and the resulting mixture was stirred at room temperature for one hour. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over anhydrous sodium sulfate and then distilled off under reduced pressure. The residue was separated and purified by a silica gel column (chloroform:n-hexane=50:1), whereby 1-{2-(2,4-difluorophenyl)-3,3-difluoro-2-methoxy-3-[(2-methoxyethyl)thio]propyl}-1H-1,2,4-triazole (894 mg, yield: 86.0%) was obtained as a yellow oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for one hour
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled off under reduced pressure
  6. customThe residue was separated
  7. custompurified by a silica gel column (chloroform:n-hexane=50:1)

Sources & evidence

ORD record
ord-5cb89934503c4299839ed84cab57d1a1
Source dataset
uspto-grants-1999_12
Patent number
US06008239

Reaction notes

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