Sodium Hydroxide → 4-(1H-1,2,4-triazol-1-yl)benzamide

2,6-Dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)aniline (0.45 g) was dissolved in pyridine (5 ml). To the solution, the crude product of 4-(1H-1,2,4-triazol-1-yl)benzoyl chloride (0.45 g) was added and the mixture was refluxed under heating for 1.5 hours. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with 2N hydrochloric acid and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a residue, which were then dissolved in tetrahydrofuran (20 ml), added with a 2N sodium hydroxide solution (5 ml) and stirred under heating at 50° C. for 2 hours. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with water and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain N-[2,6-d]bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-(1H-1,2,4-triazol-1-yl)benzamide (0.18 g, yield 28%).

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 1.5 hours
3. extractionextracted twice with ethyl acetate
4. washwashed with 2N hydrochloric acid
5. dry with materialdried over magnesium sulfate
6. filtrationAfter filtering off the drying agent
7. distillationthe solvent was distilled off under reduced pressure
8. customto obtain a residue, which
9. temperatureunder heating at 50° C. for 2 hours
10. temperatureAfter cooling to room temperature
11. extractionextracted twice with ethyl acetate
12. washwashed with water
13. dry with materialdried over magnesium sulfate
14. filtrationAfter filtering off the drying agent
15. distillationthe solvent was distilled off under reduced pressure
16. customto obtain a crude product
17. customThe crude product was purified by column chromatography

ORD record

ord-551b944f0d004f0598bb772b655bf9aa

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227923B2