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

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.

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)

ORD record

ord-5cb89934503c4299839ed84cab57d1a1

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008239