Urea → 3-Methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline

HRID 34553

Reaktionsgleichung

Reaktionsgleichung von HRID 34553
[CH3:1][NH:2][C:3]([N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[C:6]1=[O:7])=[O:4].C1CCN2C(=NCCC2)CC1.[NH2:27][C:28]([NH2:30])=[O:29]>O1CCCC1>[CH3:1][N:2]1[C:8]([OH:9])([C:6]([NH:27][C:28]([NH2:30])=[O:29])=[O:7])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:5][C:3]1=[O:4]

Komponenten

5

Edukt 3

HCID 1176UreaHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2835543N-(methylcarbamoyl)isatin

Produkt 1

HCID 142299933-Methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Methylcarbamoylisatin (10.2 g) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.3 g) are dissolved in tetrahydrofuran (100 ml), and thereto is added urea (4.5 g), and the mixture is refluxed for 10 hours. After cooling, the precipitates are taken by filtration, washed with water and methanol and recrystallized from a mixture of dimethylsulfoxide and ethanol to give 3-methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline, M.p.>280° C.,

Aufarbeitung

  1. temperaturethe mixture is refluxed for 10 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitates are taken by filtration
  4. washwashed with water and methanol
  5. customrecrystallized from a mixture of dimethylsulfoxide and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ee11b7a4037446ff838830f2b1b77ab6
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762839

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