Sodium Azide → 2-(Azidomethyl)-1,3-difluorobenzene

HRID 541030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541030
[CH:1]1[CH:2]=[C:3]([F:17])[C:4]([CH2:8][N:9]2[N:13]=[N:12]C(C(N)=O)=C2)=[C:5]([F:7])[CH:6]=1.FC1C=CC=C(F)C=1CCl.[N-]=[N+]=[N-].[Na+]>CS(C)=O>[F:7][C:5]1[CH:6]=[CH:1][CH:2]=[C:3]([F:17])[C:4]=1[CH2:8][N:9]=[N+:13]=[N-:12]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 129228RufinamideHCID 5815702,6-Difluorobenzyl chloride

Produkt 1

HCID 108883232-(Azidomethyl)-1,3-difluorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

The process comprises the preparation of Rufinamide by reacting 2,6-difluorobenzyl chloride and sodium azide in the presence of DMSO to obtain 2,6-difluoro benzyl azide, which is then treated with propiolic acid to give carboxylic acid intermediate which on further reaction with thionyl chloride to give corresponding acyl chloride. The acyl chloride intermediate is further reacted with methanolic ammonia to yield Rufinamide.

Quellen und Nachweise

ORD-Eintrag
ord-e0f8f2ef8757448e9280c2a58b32364a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871945B2

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