Reaktion #449607

ord-84d6247dfcec4af4a94acb1aa66845ee

Reaktionsgleichung

O=S(=O)([O-])[O-].[Mg+2]
MgSO4
Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccccc3Cc3ccccc32)cc1
N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-methylbenzamide
[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
→
Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccccc3C(=O)c3ccccc32)cc1
residue
Ausbeute 107.6%
Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccccc3C(=O)c3ccccc32)cc1
N-[4-[(6,11-Dihydro-11-oxo-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-methylbenzamide
Ausbeute 107.6%

Edukte

O=S(=O)([O-])[O-].[Mg+2]
MgSO4
Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccccc3Cc3ccccc32)cc1
N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-methylbenzamide
[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4

Reagenzien

Keine

Lösungsmittel

O
water
CC(C)(C)O
t-butanol
O
water

Reaktionsbedingungen

Temperatur
65°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturis heated
  2. 2
    FiltrationThe reaction mixture is filtered
  3. 3
    Sonstigethe filtrate evaporated in vacuo

Vorschrift

A mixture of 1.08 g of N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-methylbenzamide 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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05869483uspto-grants-1999_02