Dimethylformamide → 1-[[(o-Tolylamino)carbonyl]amino]-1,4-dihydro-2,3-quinoxalinedione

HRID 54341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54341
C(C[N:5]1[C:14]2[C:9](=[CH:10][C:11](Br)=[C:12](Br)[CH:13]=2)[NH:8][C:7](=[O:17])[C:6]1=[O:18])(O)=O.[N+]([C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])([O-])=O.[CH2:29]1CCC(N=C=NC2CCCCC2)CC1.C[N:45]([CH:47]=[O:48])C>>[C:26]1([CH3:29])[CH:27]=[CH:28][CH:22]=[CH:23][C:24]=1[NH:25][C:47]([NH:45][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:17])[C:6]1=[O:18])=[O:48]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 74233-NitroanilineHCID 10868DicyclohexylcarbodiimideHCID 199585561-Carboxymethyl-6,7-dibromo-1,4-dihydroquinoxaline-2,3-dione

Produkt 1

HCID 199585841-[[(o-Tolylamino)carbonyl]amino]-1,4-dihydro-2,3-quinoxalinedione

Reaktionsbedingungen

Temperatur
28 °C

Versuchsvorschrift

To a stirred solution of N-carboxymethyl-6,7-dibromo-1,4-dihydroquinoxaline-2,3-dione (100 mg, 0.260 mmol) and m-nitroaniline (40 mg, 0.29 mmol) in dry DMF (2 mL) under N2 at 28° C., DCC (60 mg, 0.29 mmol) was added in one portion. The solution was stirred for 4 h at 28° C. The insoluble solid was filtered and washed with DMF (1 mL). The clear filtrate was then poured into water (30 mL). The precipitated solid was filtered and dried under vacuum (water aspirator) to obtain 65 mg crude product as a yellow powder. The product was purified by Soxhlet extraction in boiling ethanol (20 mL), keeping the oil bath temperature at 120° C., for 4 h. The insoluble material (in the thimble) was dried under vacuum to obtain 30 mg pure (1H NMR) N-(N'-(m-nitrophenyl)carboxamidyl)-methyl-6,7-dibromo-1,4-dihydroquinox-aline-2,3-dione as a white solid (some of the product also ends up being extracted by hot ethanol which accounts for the low yield of pure product). M.p.>300° C. (decomposes). 1H NMR: δ4.98 (s, 1H), 7.45 (s, 1H), 7.61 (d of d seen as a t, J=8.1 Hz) 7.79 (s, 1H), 7.86 (d, 1H, J=9 Hz), 7.91 (d, 1H, J=8.4 Hz), 8.54 (s, 1H), 10.76 (s, 1H), 12.28 (s, 1H). IR (KBr, cm-1): 3444, 3289, 1707, 1686, 1672, 1602. HRMS: Calculated for C16H10Br2N4O5, 495.9018; Observed, 495.9008.

Aufarbeitung

  1. filtrationThe insoluble solid was filtered
  2. washwashed with DMF (1 mL)
  3. additionThe clear filtrate was then poured into water (30 mL)
  4. filtrationThe precipitated solid was filtered
  5. dry with materialdried under vacuum (water aspirator)
  6. customto obtain 65 mg crude product as a yellow powder
  7. customThe product was purified by Soxhlet extraction
  8. customat 120° C.
  9. waitfor 4 h
  10. customThe insoluble material (in the thimble) was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-65e392a454b74c988f771e2a48793d3f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622952

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