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

HRID 1927185Notes

Reaction equation

HRID 1927185 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4]Cl.[N-:11]=[N+:12]=[N-:13].[Na+]>CS(C)=O>[N:11]([CH2:4][C:3]1[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:6]=1[F:10])=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 5815702,6-Difluorobenzyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,6-difluorobenzylchloride of formula II and sodium azide are reacted in the presence of DMSO to obtain 2-(azidomethyl)-1,3-difluorobenzene of formula III, which is then treated with 2-propiolic acid to give a carboxylic acid intermediate which on further reaction with methanol in the presence of sulfuric acid yields methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate intermediate of formula IV. This intermediate is then isolated and further reacted with methanolic ammonia to yield rufinamide of formula I.

Sources & evidence

ORD record
ord-1387672bc8d84c40a2dbcc940daf5423
Source dataset
uspto-grants-2012_05
Patent number
US08183269B2

Reaction notes

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