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

HRID 53752

Reaktionsgleichung

Reaktionsgleichung von HRID 53752
C(C[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])(O)=O.[CH:17]1[C:22]([NH2:23])=[CH:21][CH:20]=[C:19](N)[CH:18]=1.[CH2:25]1CCC(N=C=NC2CCCCC2)CC1.C[N:41]([CH:43]=[O:44])C>>[C:17]1([CH3:25])[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=1[NH:23][C:43]([NH:41][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])=[O:44]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 7814P-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 129386642-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acid

Produkt 1

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

Reaktionsbedingungen

Temperatur
28 °C

Versuchsvorschrift

To a stirred solution of acid N-carboxymethyl-1,4-dihydroquinoxaline-2,3-dione (200 mg, 0.910 mmol) and p-phenylenediamine (98 mg, 0.91 mmol) in DMF (2 mL) under N2 at 0° C., DCC (190 mg, 0.910 mmol) was added in one portion. The solution was allowed to warm to 28° C. and stirred at that temperature overnight. The precipitated solid was filtered and the clear filtrate was poured into water (10 mL). The solid thus obtained was filtered and dried under vacuum (water aspirator) to obtain 180 mg crude product as a brown 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 135 mg pure (1H NMR) N-(N'-(p-aminophenyl)carboxamidyl)methyl-1,4-dihydroquinoxaline-2,3-dione as a white powder. M.p. >300° C. (decomposes). 1H NMR: δ 4.84 (s, 2H), 4.93 (s,2H), 6.5 (d, 2H, J=8.4 Hz), 7.15-7.25 (m, 6H), 9.83 (s, 1H), 12.15 (s, 1H). IR (KBr, cm-1): 3462, 3143, 1793, 1693, 1593, 1443. HRMS: Calculated for C16H14N4O3, 310.1066; Observed, 310.1071.

Aufarbeitung

  1. filtrationThe precipitated solid was filtered
  2. additionthe clear filtrate was poured into water (10 mL)
  3. customThe solid thus obtained
  4. filtrationwas filtered
  5. dry with materialdried under vacuum (water aspirator)
  6. customto obtain 180 mg crude product as a brown 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-fae12e89ba3a4d22aea0c38432ce4d1a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620979

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