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

HRID 355878

反応式

HRID 355878 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5f309f1249e14c1b99ecad4da7649a8b
出典データセット
uspto-grants-1998_11
特許番号
US05834461

関連ノート

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