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

HRID 9717

Reaktionsgleichung

Reaktionsgleichung von HRID 9717
[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.C(#N)C.[O:21]([C:23]#[N:24])[Na].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[CH3:1][O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:23]([NH2:24])=[O:21])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 7842410-Methoxyiminostilbene2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 178418852HCID 178418852, Verbindung

Produkt 1

HCID 12003110-methoxy-5H-dibenz(b,f)azepine-5-carboxamideAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

10-methoxy-5H-dibenz(b,f)azepine (29.9 g, 0.134 mol) was added to 300 ml acetonitrile in a three-neck flask (500 ml) equipped with a mechanical stirring apparatus. The mixture was stirred at room temperature for 15 minutes, and then NaOCN (18 g, 0.277 mol) was added, followed by pyridinium p-toluenesulfonate (75 g, 0.3 mol). The mixture was stirred at room temperature for about 4 hours, at which time TLC indicated that the reaction was complete (disappearance of 10-methoxy-5H-dibenz(b,f)azepine). 30 ml water was added, and the mixture stirred for 15 minutes. The solids were filtered and the filtrate was concentrated under vacuum. The semi-solid residue was triturated with acetone to provide a creamy solid, which was dried at 80° C. to provide 18 g (0.068 mol, 50% yield) of 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide (10-methoxycarbamazepine).

Aufarbeitung

  1. customequipped with a mechanical stirring apparatus
  2. stirringThe mixture was stirred at room temperature for about 4 hours, at which time TLC
  3. stirringthe mixture stirred for 15 minutes
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe semi-solid residue was triturated with acetone
  7. customto provide a creamy solid, which
  8. customwas dried at 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-ce0dd8900c0f4904b3ae6c61be0151bc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091339B2

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