反应详情

0.45 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyloxy)pyrazole was dissolved in 5 mL of N,N-dimethylformamide, the solution was dropwise added to a suspension having 40 mg of sodium hydride suspended in 10 mL of N,N-dimethylformamide under cooling with ice, and after completion of the dropwise addition, stirring was carried out at room temperature for 30 minutes. The reaction solution was cooled with ice again, and 0.15 g of methyl iodide was added, followed by stirring at room temperature for one hour. Then, water was injected, extraction with ethyl acetate was carried out, followed by washing with water, and the organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, the obtained residue was dissolved in 10 mL of ethanol, and 10 mL of a 35 mass % hydrochloric acid aqueous solution was added, followed by stirring under reflux with heating for one hour. Then, the reaction mixture was poured into water, extraction with ethyl acetate was carried out, followed by washing with water, and the organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 0.39 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-methylamino-3-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyloxy)pyrazole.

1. additionthe solution was dropwise added to a suspension
2. temperatureunder cooling with ice
3. additionafter completion of the dropwise addition
4. temperatureThe reaction solution was cooled with ice again
5. stirringby stirring at room temperature for one hour
6. extractionextraction with ethyl acetate
7. washby washing with water
8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
9. distillationThen, the solvent was distilled off under reduced pressure
10. dissolutionthe obtained residue was dissolved in 10 mL of ethanol
11. addition10 mL of a 35 mass % hydrochloric acid aqueous solution was added
12. stirringby stirring
13. temperatureunder reflux
14. temperaturewith heating for one hour
15. additionThen, the reaction mixture was poured into water, extraction with ethyl acetate
16. washby washing with water
17. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
18. distillationThen, the solvent was distilled off under reduced pressure
19. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)