Sodium Azide → 4-Chloro-3-cyanobenzyl azide
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationfiltered
- customthe filtrate was evaporated under vacuum
- customThe residue was triturated with diethyl ether
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-3c891f33b847442097777ea209d70180
- Source dataset
- uspto-grants-1988_01
- Patent number
- US04721791
Reaction notes
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