반응 #81999

반응 방정식

diethyl oxalate

4,5-difluoro-1,2-diaminobenzene

→

title compound

6,7-Difluoro-1,4-dihydro-2,3-quinoxalinedione

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux under N2 for 2 h
3. 3
   여과the solid collected by vacuum filtration
4. 4
   세척rinsed with hexanes and air
5. 5
   기타dried
6. 6
   기타This gray brown solid was recrystallized from 20 ml of EtOH
7. 7
   여과the brown-white crystals collected by vacuum filtration
8. 8
   기타the crystals further dried under vacuum (0.5 torr, 25° C.)
9. 9
   기타to yield 45.3 mg (30.0%) mp >360° C. (lit. >310° C.)

실험 절차

The title compound (Sarges, R. et al., J. Med. Chem. 33: 2240 (1990)) was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (1.11 g, 7.63 mmol and 4,5-difluoro-1,2-diaminobenzene (110 mg, 0.763 mmol) was heated to reflux under N2 for 2 h. The reaction was allowed to cool to room temperature and the solid collected by vacuum filtration and rinsed with hexanes and air dried. This gray brown solid was recrystallized from 20 ml of EtOH and the brown-white crystals collected by vacuum filtration and the crystals further dried under vacuum (0.5 torr, 25° C.) to yield 45.3 mg (30.0%) mp >360° C. (lit. >310° C.). 1H NMR (d6 -acetone) δ 7.19 (t, 2H, ArH, JH-F =9.3), 10.9 (br s, 2H, NH).

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