10-Methoxyiminostilbene → 10-methoxy-5H-dibenz(b,f)azepine-5-carboxamide

HRID 2216930

Reaktionsgleichung

Reaktionsgleichung von HRID 2216930
[CH3:1][O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[O:18]([C:20]#[N:21])[Na]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:20]([NH2:21])=[O:18])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 7842410-MethoxyiminostilbeneHCID 178418852HCID 178418852, Verbindung

Produkt 1

HCID 12003110-methoxy-5H-dibenz(b,f)azepine-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Acetic acid (150 mL) is added dropwise to a stirred mixture of 10-methoxy-5H-dibenzo[b,f]azepine (25.0 g, 112 mmol) and NaOCN (9.25 g, 142 mmol) under a nitrogen atmosphere at room temperature. After stirring for 7 hours the resulting yellow suspension of the title compound (>95% area of the compound by HPLC) is used for synthesis of 10-oxo-10,11-dihydro-dibenzo[b,f]azepine-S-carboxylic acid amide. The title compound can be isolated by adding 1N NaOH to a pH of ≧8 followed by extraction with toluene. Drying of the combined organic layers and concentration in vacuo yields the title compound as a light yellow solid (yield≧75%).

Quellen und Nachweise

ORD-Eintrag
ord-ea9860e5fa694a7994d04f4587d4f072
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112673B2

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