Sodium Azide → 2-(Azidomethyl)benzonitrile

HRID 1512253Notes

Reaction equation

HRID 1512253 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Na+]>CC(C)=O>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 114919742-(Azidomethyl)benzonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromomethyl-benzonitrile (300 mg, 1.53 mmol) and sodium azide (129 mg, 1.99 mmol) in acetone was stirred overnight at rt. The solvent was removed, and the resulting residue was chromatographed using hexane/ethyl acetate (6:1) to give the title compound (212 mg, 88%). MS (DCI/NH3) m/z 176 (M+18)+. 1HNMR (400 MHz, DMSO-d6) δ ppm 4.69 (s, 2H) 7.58 (td, J=7.67, 1.23 Hz, 1H) 7.66 (d, J=7.67 Hz, 1H) 7.76 (td, J=7.67, 1.23 Hz, 1H) 7.91 (dd, J=7.67, 1.53 Hz, 1H).

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was chromatographed

Sources & evidence

ORD record
ord-f75a8264cb724cea8a0599b92c717564
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

Loading…