Diethyl Oxalate → 6,7-Difluoroquinoxaline-2,3(1H,4H)-dione

HRID 1068589

Reaktionsgleichung

Reaktionsgleichung von HRID 1068589
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[F:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([NH2:19])=[C:14]([NH2:20])[CH:13]=1>>[F:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][C:17]=1[F:18])[NH:19][C:1](=[O:8])[C:2](=[O:4])[NH:20]2

Komponenten

3

Edukt 2

HCID 7268Diethyl OxalateHCID 27367551,2-Diamino-4,5-difluorobenzene

Produkt 1

HCID 8228396,7-Difluoroquinoxaline-2,3(1H,4H)-dione

Versuchsvorschrift

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. Cam. 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 was collected by vacuum filtration, 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).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 2 h
  3. filtrationthe solid was collected by vacuum filtration
  4. washrinsed with hexanes, and air
  5. customdried
  6. customThis gray brown solid was recrystallized from 20 mL of EtOH
  7. filtrationthe brown-white crystals collected by vacuum filtration
  8. customthe crystals further dried under vacuum (0.5 torr, 25° C.)
  9. customto yield 45.3 mg (30.0%)
  10. custommp >360° C. (lit. >310° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f3301b631ce841988542bc08c9a97de0
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251903B1

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