反应详情

温度

100 °C

A mixture of methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate (13.4 g, 0.0580 mol), phosphoryl chloride (30 mL, 0.3 mol) in chloroform (50 mL) was heated at reflux (oil-bath temperature about 100° C.) for 2 h. After cooling, the mixture was concentrated to remove excess phosphoryl chloride. The residue was dissolved in DCM. The solution was poured into ice-water, and carefully neutralized with K2CO3. The organic layer was separated. The aqueous solution was extracted with methylene chloride. The combined extracts were dried over Na2SO3. After filtration the filtrate was concentrated and further purified by flash column to afford the desired product (2.5 g, 17%). Analytical LCMS: (M+H)+=249.9. 1H NMR (300 MHz, CDCl3): δ(ppm) 3.98 (s, 3H), 8.18 (d, 2H), 8.24 (d, 2H), 8.96 (s, 1H).

1. temperaturewas heated
2. temperatureAfter cooling
3. concentrationthe mixture was concentrated
4. customto remove excess phosphoryl chloride
5. dissolutionThe residue was dissolved in DCM
6. additionThe solution was poured into ice-water
7. customThe organic layer was separated
8. extractionThe aqueous solution was extracted with methylene chloride
9. dry with materialThe combined extracts were dried over Na2SO3
10. filtrationAfter filtration the filtrate
11. concentrationwas concentrated
12. customfurther purified by flash column