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

HRID 355878

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-5f309f1249e14c1b99ecad4da7649a8b
Quelldatensatz: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05834461

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