Sodium Azide → 4-(Azidomethyl)benzonitrile

HRID 2290025Notes

Reaction equation

HRID 2290025 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.O>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 110736914-(Azidomethyl)benzonitrileYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(bromomethyl)benzonitrile (7.1 g) and sodium azide (2.6 g) in DMF (40 mL) is stirred for 19 hrs. The reaction mixture is then diluted with water (150 mL) and extracted with ether (2×50 mL). The organic phases are combined, washed with water (50 mL) and brine (50 mL), and dried with MgSO4. Filtration and evaporation of the solvent leaves 5.5 g of 4-(azidomethyl)benzonitrile as a clear, colorless oil.

Workup

  1. extractionextracted with ether (2×50 mL)
  2. washwashed with water (50 mL) and brine (50 mL)
  3. dry with materialdried with MgSO4
  4. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-465f582962034c35b33c7efde8967bee
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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