Sodium Azide → 4-(Azidomethyl)benzonitrile

HRID 1355606Notes

Reaction equation

HRID 1355606 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]>CN(C=O)C.O>[N:1]([CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:5]#[N:6])=[CH:8][CH:9]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 110736914-(Azidomethyl)benzonitrileYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium azide (Aldrich, 3.5 g, 54 mmol) was added to a solution of p-cyanobenzyl bromide (Aldrich, 10 g, 51 mmol) in DMF (100 ml), and the resulting mixture was stirred at ambient temperature for 5 hours. The reaction mixture was then diluted with water (350 ml) and extracted with ether (2×100 ml). Combined organic layers were washed with brine and dried (MgSO4). Removal of solvent gave the title compound (8 g, 96%). 1H NMR (CDCl3): δ 4.42 (s, 2H), 7.41 (d, 2H, J=8.1 Hz), 7.65 (d, 2H, J=8.1 Hz).

Workup

  1. extractionextracted with ether (2×100 ml)
  2. washCombined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-4a057c361822411eb0befe7d3c5be166
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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