Water → 4-(Azidomethyl)benzonitrile

HRID 35920

Reaction equation

HRID 35920 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-c905a16c14b340969660360c09b93391
Source dataset
uspto-grants-1995_05
Patent number
US05411982

Linked notes

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