Sodium Azide → 2-(Azidomethyl)benzonitrile

HRID 1035000Notes

Reaction equation

HRID 1035000 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)+. 1H NMR. (400 MHz, DMSO-d6) δ ppm 4.69 (s, 2 H) 7.58 (td, J=7.67, 1.23 Hz, 1 H) 7.66 (d, J=7.67 Hz, 1 H) 7.76 (td, J=7.67, 1.23 Hz, 1 H) 7.91 (dd, J=7.67, 1.53 Hz, 1 H).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-8415d79c5c5a40948ee7a02821a66db5
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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