反应详情

Anhydrous zinc chloride (0.136 g, 1.0 mmol) was fused with a nitrogen purge in a round bottom flask with an open flame. The reaction vessel was allowed to return to ambient temperature, then dioxane (10 mL) was added. To this mixture was added 6-fluoro-2-methyl-3-(2-methyl-phenyl)-3H-quinazolin-4-one (0.1 34 g, 0.5 mmol), acetic anhydride (0.141 mL, 1.5 mmol), and 2-methylthiazole-4-carboxaldehyde (0.191 g, 1.5 mmol). The reaction was refluxed 3.5 hours, at which time the reaction was allowed to cool to ambient temperature. Once the reaction had cooled to ambient temperature it was diluted with water. The resulting mixture was repeatedly extracted with chloroform. The chloroform extracts were combined and the resulting chloroform layer was washed with water and brine, dried over sodium sulfate and concentrated to leave a dark residue. This residue was triturated with ether, filtered and dried to afford 0.04 g (21%) of 6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-3H-quinazolin-4-one as a tan solid.

1. custompurge in a round bottom flask with an open flame
2. customto return to ambient temperature
3. additiondioxane (10 mL) was added
4. temperatureThe reaction was refluxed 3.5 hours, at which time the reaction
5. temperatureOnce the reaction had cooled to ambient temperature it
6. extractionThe resulting mixture was repeatedly extracted with chloroform
7. washthe resulting chloroform layer was washed with water and brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customto leave a dark residue
11. customThis residue was triturated with ether
12. filtrationfiltered
13. customdried