Sodium Azide → 2-(Azidomethyl)benzonitrile

HRID 2240352Notes

Reaction equation

HRID 2240352 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 chromatographered 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

Sources & evidence

ORD record
ord-f4083d17de1140dda3d7857d71359a64
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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