Water → 2-(1H-1,2,4-triazol-1-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzonitrile

温度

-5 °C

methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate (0.2 g) and 1,2,3-trichloro-5-[1-(trifluoromethyl)ethenyl]benzene (0.17 g) were dissolved in THF and cooled to −5° C. to be stirring. Additionally a solution of tetrabutylammonium fluoride (0.099 mL of 1.0 M in THF) in THF was added over 10 minutes under argon atmosphere. The reaction mixture was stirred for 30 minutes at the same temperature and returned to room temperature gradually, and then stirred 4 hours. Water was added to the reaction liquor, and aqueous layer was extracted with ethyl acetate. The combined organic layers, were washed with a saturated aqueous brine, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 2-(1H-1,2,4-triazol-1-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzonitrile (0.25 g) at a yield of 85%.

1. stirringThe reaction mixture was stirred for 30 minutes at the same temperature
2. customreturned to room temperature
3. stirringstirred 4 hours
4. extractionwas extracted with ethyl acetate
5. washThe combined organic layers, were washed with a saturated aqueous brine
6. dry with materialsubsequently dried over magnesium sulfate
7. filtrationAfter filtering the reaction mixture
8. distillationthe solvent was distilled off under reduced pressure
9. customthe resulting mixture was purified by silica gel chromatography

ORDレコード

ord-91224d66d7c2418e96285d146f3bd598

出典データセット

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08304371B2