Sodium Azide → 4-Azidomethyl-3-chlorobenzonitrile

HRID 896245Notes

Reaction equation

HRID 896245 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:3]=1[CH2:4][N:12]=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 130420934-(Bromomethyl)-3-chlorobenzonitrile

Product 1

HCID 223499744-Azidomethyl-3-chlorobenzonitrileYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-choro-4-cyanobenzyl bromide (6.9 g, 30.0 mmol) in DMF (150 ml), was added sodium azide (2.0 g, 30 mmol) The reaction was stirred overnight at room temperature, and then filtered. The DMF was removed from filtrate in vacuo. The residue was dissolved in EtOAc (300 ml), washed with water (200 ml×3), brine (200 ml×1), dried over sodium sulfate. Removed solvent in vacuo to give 5.8 g of raw 2-choro-4-cyanobenzyl azide.

Workup

  1. filtrationfiltered
  2. customThe DMF was removed from filtrate in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (300 ml)
  4. washwashed with water (200 ml×3), brine (200 ml×1)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-c892a0b602544be0bc4b0e6805f9da90
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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