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

HRID 362375Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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 (Na2SO4) 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.

Workup

temperatureThe mixture is refluxed for 2 hours
filtrationfiltered
additionTo the filtrate is added 1N HCl
filtrationthe mixture filtered
dry with materialThe filtrate is dried (Na2SO4)
customthe solvent removed
customto give a solid
customThe solid (1.1 g) is chromatographed on thick layer silica gel plates

Sources & evidence

ORD record: ord-ec6771f4acfd45788d7e0c97670434ff
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869483

Reaction notes

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