Toluene → 3-(6H-Dibenzo[b,e]oxepin-1-ylidenemethyl)-phenylamine

HRID 2218732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2218732
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH:7]=[C:8]1O[C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)([O-])=O.[OH2:26].O.[Sn](Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>C(O)C.C(OCC)(=O)C>[C:8]1(=[CH:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:25]=[CH:24][CH:23]=2)[C:9]2[C:22]([O:26][CH2:13][C:15]3[CH:16]=[CH:17][CH:18]=[CH:12][C:11]=3[CH:10]=2)=[CH:21][CH:20]=[CH:19]1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 85782573Tin tetrachloride dihydrateHCID 866039843-Nitro-benzylidene-6,11-dihydro-dibenzo[b,e]oxepine

Produkt 1

HCID 866039833-(6H-Dibenzo[b,e]oxepin-1-ylidenemethyl)-phenylamineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolve 11-(3-Nitro-benzylidene-6,11-dihydro-dibenzo[b,e]oxepine (200 mg) in ethanol (10 mL) add tin chloride dihydrate (680 mg) and reflux for 5 h. Concentrate the reaction in vacuo, re-dissolve in ethyl acetate and wash with 1N sodium hydroxide solution. Separate the layers wash with brine and dry over sodium sulfate. Purity using filter chromatography eluting with 10% ethyl acetate:toluene to give 60 mg of product (56% yield).

Aufarbeitung

  1. temperaturereflux for 5 h
  2. concentrationConcentrate
  3. customthe reaction in vacuo
  4. washwash with 1N sodium hydroxide solution
  5. customSeparate the layers
  6. washwash with brine
  7. dry with materialdry over sodium sulfate
  8. filtrationPurity using filter chromatography
  9. washeluting with 10% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2cffb80652e44e01aaa6a3839092257b
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07411072B2

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