反应详情

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (0.50 g, 1.9 mmol) in acetonitrile (10 mL) was added diphenylmethylamine (0.39 g, 2.1 mmol) and triethylamine (0.29 g, 2.4 mmol), and this was heated to reflux for 10 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To the residue obtained was added iron powder (0.33 g, 5.8 mmol), and aqueous acetic acid (50 mL), and this was heated to reflux for 2 hours. After cooling the reaction solution, filtration through Celite and concentration, the residue obtained was purified by silica gel column chromatography. The oil obtained was dissolved in tetrahydrofuran (3 mL), and to this was added a 1M solution of hydrogen chloride in diethyl ether (1 mL). The precipitated crystals were filtered, and after washing with tetrahydrofuran, they were dried to yield the title compound (0.15 g, 20% yield) as a light brown solid.

1. temperaturethis was heated
2. temperatureto reflux for 10 hours
3. filtrationthe precipitated crystals were filtered
4. washwashed with water
5. customdried
6. customTo the residue obtained
7. temperaturethis was heated
8. temperatureto reflux for 2 hours
9. temperatureAfter cooling
10. filtrationthe reaction solution, filtration
11. concentrationthrough Celite and concentration
12. customthe residue obtained
13. customwas purified by silica gel column chromatography
14. customThe oil obtained
15. filtrationThe precipitated crystals were filtered
16. washafter washing with tetrahydrofuran, they
17. customwere dried