반응 #610403

반응 방정식

2-amino-N-(3-bromo-2-methylphenyl)-5-fluorobenzamide

triphosgene

NaHCO3

→

3-(3-bromo-2-methylphenyl)-6-fluoroquinazoline-2,4(1H,3H)-dione

수율 87.7%

용매

THF

반응 조건

후처리

1. 1
   추출The mixture was extracted twice with DCM
2. 2
   세척The combined organic phases were washed with water
3. 3
   기타dried
4. 4
   농축concentrated
5. 5
   기타The residue was triturated with DCM
6. 6
   기타to give a white solid
7. 7
   기타isolated by filtration
8. 8
   농축The filtrate was concentrated
9. 9
   세척eluting with EtOAc-hexanes (gradient from 0-80%)
10. 10
    기타to provide additional solid

실험 절차

A solution of 2-amino-N-(3-bromo-2-methylphenyl)-5-fluorobenzamide (0.893 g, 2.76 mmol) and triphosgene (0.984 g, 3.32 mmol) in THF (30 mL) was stirred at room temperature for 2 h. The mixture was carefully treated with saturated aqueous NaHCO3 and stirred until gas evolution ceased. The mixture was extracted twice with DCM. The combined organic phases were washed with water, dried and concentrated. The residue was triturated with DCM to give a white solid, isolated by filtration. The filtrate was concentrated and subjected to column chromatography on silica gel (40 g), eluting with EtOAc-hexanes (gradient from 0-80%), to provide additional solid. The two solids were combined to provide 3-(3-bromo-2-methylphenyl)-6-fluoroquinazoline-2,4(1H,3H)-dione as a white solid (845 mg, 87% yield). Mass spectrum m/z 349, 351 (M+H)+.

출처