Sodium Azide → 4-Chloro-3-cyanobenzyl azide

HRID 1194717Notes

Reaction equation

HRID 1194717 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-2d9efaf094644f2fb1db6891b7fc2a98
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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