1,4-Dioxane → 7-Benzyloxy-6-methoxy-3H-quinazolin-4-one

HRID 495379Notes

Reaction equation

HRID 495379 reaction equation
[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].[Cl-].[CH3:22]N(C)C=NC=[N+](C)C.O1CCOCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:12]([O:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][CH:22]=[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

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 11008255Gold's ReagentHCID 124714802-Amino-4-(benzyloxy)-5-methoxybenzamide

Product 1

HCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-oneYield 83.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (J. Med. Chem. 1977, 20, 146-149; 10 g), (3-dimethylamino-2-azaprop-2-en-1-ylidene)dimethylammonium chloride (Gold's reagent, 7.4 g) and dioxane (100 ml) was stirred and heated to reflux for 24 hours. Sodium acetate (3.02 g) and acetic acid (1.65 ml) were added and the reaction mixture was heated for a further 3 hours. The mixture was evaporated and water was added to the residue. The resultant solid was collected by filtration, washed with water and dried. The material was recrystallised from acetic acid to give 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (8.7 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperaturethe reaction mixture was heated for a further 3 hours
  4. customThe mixture was evaporated
  5. additionwater was added to the residue
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customThe material was recrystallised from acetic acid

Sources & evidence

ORD record
ord-eb4c40049b1e45e9ababfa0604785b56
Source dataset
uspto-grants-2005_09
Patent number
US06939866B2

Reaction notes

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