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

HRID 541030Notes

Reaction equation

HRID 541030 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Sources & evidence

ORD record
ord-e0f8f2ef8757448e9280c2a58b32364a
Source dataset
uspto-grants-2014_10
Patent number
US08871945B2

Reaction notes

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