Water → HCID 10569788, compound

HRID 2287444Notes

Reaction equation

HRID 2287444 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:24])([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:12]([S:15][CH2:16][CH3:17])([F:14])[F:13].[CH3:25]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:24][CH3:25])([C:12]([S:15][CH2:16][CH3:17])([F:14])[F:13])[CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10664501HCID 10664501, compound

Product 1

HCID 10569788HCID 10569788, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 60% sodium hydride (0.16 g, 4.0 mmol) in N,N-dimethylformamide (50 ml), 2-(2,4-difluorophenyl)-1-(ethylthio)-1,1-difluoro-3-(1H-1,2,4-triazole-1-yl)-2-propanol (1.0 g, 3.0 mmol) was added dropwise under ice cooling, followed by stirring at room temperature for 30 minutes. Methyl iodide (0.56 g, 3.9 mmol) was then added dropwise to the reaction mixture under ice cooling and the resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with ether. The ether solution was washed with water and dried over sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected to a silica gel column and from the chloroform eluate fraction, 1-[2-(2,4-difluorophenyl)-3-ethylthio-3,3-difluoro-2-methoxypropyl]-1H-1,2,4-triazole (0.81 g, yield: 78%) was obtained as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. extractionfollowed by extraction with ether
  3. washThe ether solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-8e89cf293dcb47d7add12956e4c127b4
Source dataset
uspto-grants-2000_07
Patent number
US06083968

Reaction notes

Loading…