Sodium Azide → 4-(Azidomethyl)benzonitrile

HRID 855

Reaction equation

HRID 855 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1)#[N:6]>O.CN(C=O)C.C1(C)C=CC=CC=1>[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]=[N+:2]=[N-:3])=[CH:9][CH:8]=1)#[N:6]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 110736914-(Azidomethyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 20.23 g (0.31 mol) sodium azide in 50 ml water was added to 49.15 g (251 mmol) 4-cyanobenzyl bromide in 200 ml DMF at ambient temperature. An exothermic reaction took place and after 1.5 h the reaction mixture was diluted with 200 ml toluene(caution: In order to avoid separation of potentially explosive azide compounds it is adviceable to add the toluene to the reaction mixture before addition of the water) and 500 ml water. The aqueous phase was extracted with an additional 2×50 ml toluene. The combined organic extracts were washed with 2×50 ml water and brine and finally dried (MgSO4) and filtered. The solution was used as such in the next step.

Workup

  1. customAn exothermic reaction
  2. customseparation of potentially explosive azide compounds it
  3. additionto add the toluene to the reaction mixture
  4. additionbefore addition of the water) and 500 ml water
  5. extractionThe aqueous phase was extracted with an additional 2×50 ml toluene
  6. washThe combined organic extracts were washed with 2×50 ml water and brine
  7. dry with materialfinally dried (MgSO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-a4b47970bbbd496493b0100b353ff70e
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

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