反应详情

N-{4-[2-(3-Nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (E,Z mixture) (315 mg) in a mixed solvent of methyl alcohol (3 ml), tetrahydrofuran (6 ml), and acetic acid (1 ml) was hydrogenated over 10% Palladium on carbon (50% wet, 200 mg) under 4.3 atmospheric pressure at room temperature for 3 hours. The catalyst was removed off by filtration, and the filtrate was evaporated in vacuo. The residue was poured into water, the pH of the aqueous layer was adjusted to 9 with aqueous sodium hydrogen carbonate. The resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (9 g) using a mixed solvent of n-hexane and ethyl acetate (2:1 to 1:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give syrup. The syrup of the objective compound was changed to solid in freezer (275 mg, 96.6%).

1. customThe catalyst was removed off by filtration
2. customthe filtrate was evaporated in vacuo
3. additionThe residue was poured into water
4. extractionThe resulting mixture was extracted with ethyl acetate
5. washThe extract was washed with brine
6. dry with materialdried over magnesium sulfate
7. customevaporated under reduced pressure
8. customThe resulting residue was purified by column chromatography on silica gel (9 g)
9. additionThe fractions containing the objective compound
10. customwere collected
11. customevaporated under reduced pressure
12. customto give syrup