Sulfuric acid magnesium salt (1:1) → N-[4-[(6,11-Dihydro-11-oxo-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]-2-methylbenzamide

HRID 1957672Notes

Reaction equation

[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][N:6]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[CH:20][CH:19]=3)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[O-:34]S([O-])(=O)=O.[Mg+2].[O-][Mn](=O)(=O)=O.[K+]>C(O)(C)(C)C.O>[O:34]=[C:10]1[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH2:7][N:6]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[CH:20][CH:19]=2)=[O:17])[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]1=2

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1.08 g of N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-methyl-benzamide in 50 ml of t-butanol is heated, 2 ml of water is added followed by 1.18 g of MgSO4, and 2,6 g of KMnO4. An additional 0.84 g of KMnO4 in 25 ml of water is added followed by heating at 65° C. for 18 hours. The reaction mixture is filtered and the filtrate evaporated in vacuo to give 1.2 g of a residue which is purified by column chromatography on silica gel by elution with ethyl acetate and 9:1 ethyl acetate-methanol to give 160 mg of the desired product as a solid, m.p. 115°-119° C.

Workup

temperatureis heated
filtrationThe reaction mixture is filtered
customthe filtrate evaporated in vacuo

Sources & evidence

ORD record: ord-fe59302c251e40ec8b3013e75e40bae8
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05786353

Reaction notes

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