Reaktion #9813

Reaktionsgleichung

pyridinium p-toluenesulfonate

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

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

acetonitrile

NaOCN

→

10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide

Ausbeute 50.7%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a mechanical stirring apparatus
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for about 4 hours, at which time TLC
3. 3
   workup.STIRRINGthe mixture stirred for 15 minutes
4. 4
   FiltrationThe solids were filtered
5. 5
   Einengenthe filtrate was concentrated under vacuum
6. 6
   SonstigeThe semi-solid residue was triturated with acetone
7. 7
   Sonstigeto provide a creamy solid, which
8. 8
   Sonstigewas dried at 80° C.

Vorschrift

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).

Quelle