Iminodibenyl → N-[4-(10,11-Dihydro-dibenzo[b,f]azepine-5-carbonyl)-phenyl]-2-methyl-benzamide

HRID 355878

반응식

HRID 355878 반응식
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:5].[CH:20]1[C:30]2[CH2:29][CH2:28][C:27]3[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=3[NH:25][C:24]=2[CH:23]=[CH:22][CH:21]=1.[H-].[Na+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.ClCCl.O>[CH:20]1[C:30]2[CH2:29][CH2:28][C:27]3[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=3[N:25]([C:11]([C:10]3[CH:14]=[CH:15][C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=4[CH3:1])=[CH:8][CH:9]=3)=[O:12])[C:24]=2[CH:23]=[CH:22][CH:21]=1

참가 물질

8

반응물 3

HCID 10308IminodibenylHCID 24758Sodium hydrideHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

생성물 1

HCID 15307967N-[4-(10,11-Dihydro-dibenzo[b,f]azepine-5-carbonyl)-phenyl]-2-methyl-benzamide수율 3.2%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

To a mixture of 1.37 g (5 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 0.061 g of 4-(dimethylamino)pyridine in 4 ml of pyridine is added 0.975 g (5 mmol) of 10,11-dihydro-5H-dibenz[b,f]azepine. The mixture is heated at 80° C. for 18 hours and then 0.2 g of sodium hydride (60% in oil) (5 mmol) is added. The mixture is refluxed for 2 hours, diluted with dichloromethane and water and then filtered. To the filtrate is added 1N HCl and the mixture filtered. The filtrate is dried (Na2 SO4) and the solvent removed to give a solid. The solid (1.1 g) is chromatographed on thick layer silica gel plates to give 70 mg of yellow solid, m.p. 112°-118° C.

후처리

  1. temperatureThe mixture is refluxed for 2 hours
  2. filtrationfiltered
  3. additionTo the filtrate is added 1N HCl
  4. filtrationthe mixture filtered
  5. customThe filtrate is dried (Na2 SO4)
  6. customthe solvent removed
  7. customto give a solid
  8. customThe solid (1.1 g) is chromatographed on thick layer silica gel plates

출처 및 근거

ORD 기록
ord-5f309f1249e14c1b99ecad4da7649a8b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834461

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