反应详情

A stirred mixture of 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-phenylquinazoline (2.74 g. 0.01 mole) in dry tetrahydrofuran (150 ml.) is cooled in an ice bath, under nitrogen, and treated with dry pyridine (1.77 ml., 0.022 mole). This mixture is then treated dropwise, during 1 hour with a solution of β-phthalimidopropionyl chloride (5.23 g., 0.022 mole) in tetrahydrofuran (25 ml.). The mixture is kept in the ice bath for 1 hour and at ambient temperature for 4 hours. It is then poured into cold, dilute aqueous sodium bicarbonate and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is mixed with toluene (165 ml.), treated with trifluoroacetic acid (0.732 ml.) and warmed, under nitrogen at 100°-110° C. for 1.5 hours. The mixture is concentrated in vacuo and the residue mixed with cold water and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on silica gel (300 g) with 1.5% methanol-98.5% chloroform. The product thus obtained is crystallized to give 5-chloro-2-[3-(2-phthalimidoethyl)-4H-1,2,4-triazol-4-yl]benzophenone.

1. temperatureis cooled in an ice bath, under nitrogen
2. extractionextracted with chloroform
3. washThe extract is washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. additionThe residue is mixed with toluene (165 ml.)
7. additiontreated with trifluoroacetic acid (0.732 ml.)
8. temperaturewarmed, under nitrogen at 100°-110° C. for 1.5 hours
9. concentrationThe mixture is concentrated in vacuo
10. additionthe residue mixed with cold water
11. extractionextracted with chloroform
12. washThe extract is washed with brine
13. dry with materialdried over anhydrous sodium sulfate
14. concentrationconcentrated
15. customThe residue is chromatographed on silica gel (300 g) with 1.5% methanol-98.5% chloroform
16. customThe product thus obtained
17. customis crystallized