反应详情

温度

60 °C

A mixture of 2-[1-(4-chloro-3-nitrophenyl)ethenyl]-N-[3-(trifluoromethyl)phenyl]benzamide (0.72 g, 1.6 mmol), sodium azide (3.1 g, 4.8 mmol) and N,N-dimethylformamide (2 mL) was stirred 60° C. for 18 hours. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (3×30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated to give an oily residue. This residue was dissolved in tetrahydrofuran, cooled to 0° C. then sodium borohydride (0.11 g, 2.7 mmol) was added and stirring was continued for 30 minutes at room temperature. The reaction mixture was quenched with methanol (2 mL), concentrated then diluted with ethyl acetate (50 mL). The organic solution was washed with water (30 mL) then brine solution (30 mL) then dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 15-50% ethyl acetate-hexane) to give 2-[1-(4-amino-3-nitrophenyl)ethenyl]-N-[3-(trifluoromethyl)phenyl]benzamide (0.35 g, 0.8 mmol, 50% yield). MS (EI) for C22H16F3N3O3: 428 (MH+).

1. washwashed with water (3×30 mL), brine (30 mL)
2. dry with materialdried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. customto give an oily residue
6. temperaturecooled to 0° C.
7. stirringstirring
8. waitwas continued for 30 minutes at room temperature
9. customThe reaction mixture was quenched with methanol (2 mL)
10. concentrationconcentrated
11. additionthen diluted with ethyl acetate (50 mL)
12. washThe organic solution was washed with water (30 mL)
13. dry with materialbrine solution (30 mL) then dried over sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated
16. customThe residue was purified by flash chromatography (silica gel, eluting with 15-50% ethyl acetate-hexane)