Water → 4-Allylamino-6-nitro-2-(propylcarbamoyl)aminoquinazoline

HRID 1250596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250596
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH2:18])[N:6]=1)[CH:2]=[CH2:3].[CH2:19]([N:22]=[C:23]=[O:24])[CH2:20][CH3:21].C(N(CC)CC)C.O>C1COCC1>[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:18][C:23](=[O:24])[NH:22][CH2:19][CH2:20][CH3:21])[N:6]=1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 183264494-Allylamino-2-amino-6-nitroquinazoline

Produkt 1

HCID 183264484-Allylamino-6-nitro-2-(propylcarbamoyl)aminoquinazolineAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

After 200 mg (0.82 mmol) of 4-allylamino-2-amino-6-nitroquinazoline was dissolved in 10 ml of THF, 153 mg (1.80 mmol) of propylisocyanate and 0.13 ml (0.90 mmol) of triethylamine were added thereto, and then the reaction mixture was subjected to heating under reflux overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 218 mg (80.5%) of the title compound.

Aufarbeitung

  1. temperatureto heating
  2. temperatureunder reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-1b2d28acb524461e8e251cfc2ddcc283
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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