反应详情

After sodium (6.2 g, 268 mmol) was dissolved in ethanol (700 mL), 3-(3-fluorophenyl)-2-(4-pyridyl)-2-propene nitrile (50 g, 223 mmol) and guanidine hydrochloride (25.6 g, 268 mmol) were added thereto in this order and heated under reflux for 4 hours. After cooling as it was, the solvent was removed. Tetrahydrofuran (500 mL) was added to the residue, the insoluble matters were filtered off, and the filtrate was concentrated. A suspension of the residues and activated manganese dioxide (200 g) in chloroform (1000 mL) was heated under reflux for 2 hours. After cooling as it was, the manganese dioxide was filtered off through Celite, and washed with tetrahydrofuran (500 mL33 3) and methanol-chloroform (1:1) (1000 mL×2). The collected filtrate was concentrated, and then methanol was added to the residue. The resulting precipitates were collected by filtration, to give the title compound as a crude solid (14.6 g). The crude crystals were recrystallized from methanol-chloroform, to give the title compound (12.4 g, 20%) as a colorless solid.

1. temperaturein this order and heated
2. temperatureunder reflux for 4 hours
3. temperatureAfter cooling as it
4. customthe solvent was removed
5. additionTetrahydrofuran (500 mL) was added to the residue
6. filtrationthe insoluble matters were filtered off
7. concentrationthe filtrate was concentrated
8. additionA suspension of the residues and activated manganese dioxide (200 g) in chloroform (1000 mL)
9. temperaturewas heated
10. temperatureunder reflux for 2 hours
11. temperatureAfter cooling as it
12. filtrationthe manganese dioxide was filtered off through Celite
13. washwashed with tetrahydrofuran (500 mL33 3) and methanol-chloroform (1:1) (1000 mL×2)
14. concentrationThe collected filtrate was concentrated
15. additionmethanol was added to the residue
16. customThe resulting precipitates
17. filtrationwere collected by filtration