Chloroform → 4-{[7-(Benzyloxy)-6-methoxy-4-quinazolinyl]oxy}-2-chloroaniline

HRID 1008340

반응식

HRID 1008340 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:25]=1[Cl:31].[OH-].[Na+].C(Cl)(Cl)Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O.O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:30][C:27]3[CH:28]=[CH:29][C:24]([NH2:23])=[C:25]([Cl:31])[CH:26]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineHCID 125981904-Amino-3-chlorophenol hydrochloride

생성물 1

HCID 226672324-{[7-(Benzyloxy)-6-methoxy-4-quinazolinyl]oxy}-2-chloroaniline수율 90%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

7-(Benzyloxy)-4-chloro-6-methoxyquinazoline (30.0 g) and tetrabutylammonium chloride (13.9 g) were dissolved in acetone (400 ml), and the solution was stirred at room temperature. A solution of 4-amino-3-chlorophenol hydrochloride (36.0 g) in a 20% aqueous sodium hydroxide solution (64 ml) was added thereto. The mixture was then heated under reflux for 3 hr. The reaction solution was cooled to room temperature, and chloroform and water were added to the cooled reaction solution, followed by extraction with chloroform. The extract was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and was then dried over anhydrous sodium sulfate. Next, sodium sulfate was removed, and the solvent was then removed by distillation. The residue was washed with methanol, and the washed solid was subjected to evaporation to dryness in vacuo through a vacuum pump to give 36.6 g (yield 90%) of the title compound.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 3 hr
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionfollowed by extraction with chloroform
  5. washThe extract was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialwas then dried over anhydrous sodium sulfate
  7. customNext, sodium sulfate was removed
  8. customthe solvent was then removed by distillation
  9. washThe residue was washed with methanol
  10. customthe washed solid was subjected to evaporation to dryness in vacuo through a vacuum pump

출처 및 근거

ORD 기록
ord-2f79078892f0406ba85cbcd90b3c5a14
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06797823B1

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