Acetic Acid → 7-Benzyloxy-6-methoxy-3H-quinazolin-4-one

HRID 453980

Reaktionsgleichung

Reaktionsgleichung von HRID 453980
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH3:20])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:21]N(C=NC=[N+](C)C)C.[Cl-].C([O-])(=O)C.[Na+].C(O)(=O)C>O1CCOCC1>[CH2:12]([O:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][CH:21]=[N:1]2)=[CH:7][C:8]=1[O:19][CH3:20])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 11008255Gold's ReagentHCID 124714802-Amino-4-(benzyloxy)-5-methoxybenzamide

Produkt 1

HCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-oneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (10 g, 0.04 mol), (J. Med. Chem. 1977, vol 20, 146-149), and Gold's reagent (7.4 g, 0.05 mol) in dioxane (100 ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 0.037 mol) and acetic acid (1.65 ml, 0.029 mol) were added to the reaction mixture and it was heated for a further 3 hours. The volatiles were removed by evaporation, water was added to the residue, the solid was collected by filtration, washed with water and dried. Recrystallisation from acetic acid gave 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (8.7 g, 84%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. temperaturewas heated for a further 3 hours
  4. customThe volatiles were removed by evaporation, water
  5. additionwas added to the residue
  6. filtrationthe solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customRecrystallisation from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-74340034b4d84b30a5e55e4f32e6e17e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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