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

HRID 22771

반응식

HRID 22771 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-39555bc4030d4ec288c88a71ba08fa7f
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849625B2

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