Sodium Azide → 4-Chloro-3-cyanobenzyl azide

HRID 1709663Notes

Reaction equation

HRID 1709663 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][C:3]=1[C:10]#[N:11].[N-:12]=[N+:13]=[N-:14].[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:12]=[N+:13]=[N-:14])=[CH:4][C:3]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 140330355-(Bromomethyl)-2-chlorobenzonitrile

Product 1

HCID 230362384-Chloro-3-cyanobenzyl azideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 4-chloro-3-cyanobenzyl bromide (3.0 g, 13 mmol) and sodium azide (1.26 g, 19.4 mmol) was refluxed 5 hours in absolute ethanol (30 mL). The mixture was kept 18 hours at ambient temperature, filtered, and the filtrate was evaporated under vacuum. The residue was triturated with diethyl ether, filtered, and evaporated to provide 2.45 g (98%) liquid 4-chloro-3-cyanobenzyl azide; I.R. (neat): 2240, 2100 cm1.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f35ccbb7e93e459ab59c2fdf8f278e0e
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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