Water → 4-(Azidomethyl)benzonitrile

HRID 846084Notes

Reaction equation

HRID 846084 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+].O>CN1CCN(C)C1=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 3

HCID 962WaterHCID 33557Sodium AzideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 110736914-(Azidomethyl)benzonitrileYield 96.7%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

50 g of 4-bromomethylbenzonitrile is dissolved in 350 ml of 1,3-dimethyl-2-imidazolidinone and stirred at 25° for 2 hours with 32.5 g of sodium azide. The mixture is subsequently combined with 500 ml of water under ice cooling, extracted twice with dichloromethane, washed with water, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus obtaining 39 g of 4-azidomethylbenzonitrile as a colorless liquid.

Workup

  1. extractionextracted twice with dichloromethane
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-7b9835098a234deeb6f8033e4db95ada
Source dataset
uspto-grants-1992_08
Patent number
US05135937

Reaction notes

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