Sodium Azide → 4-Benzoyl-3,5-dichorobenzyl azide

HRID 280667Notes

Reaction equation

HRID 280667 reaction equation
[C:1]([C:9]1[C:16]([Cl:17])=[CH:15][C:12]([CH2:13]Br)=[CH:11][C:10]=1[Cl:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>C(O)C>[C:1]([C:9]1[C:16]([Cl:17])=[CH:15][C:12]([CH2:13][N:19]=[N+:20]=[N-:21])=[CH:11][C:10]=1[Cl:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 136496584-Benzoyl-3,5-dichlorobenzyl bromide

Product 1

HCID 150652124-Benzoyl-3,5-dichorobenzyl azideYield 212.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-benzoyl-3,5-dichlorobenzyl bromide (2.37 g, 6.89 mmol) and sodium azide (1.32 g, 20:3 mmol) in absolute ethanol (31 ml) was refluxed 5 hours, cooled, and evaporated. The residue was dissolved in diethyl ether and filtered. The filtrate was evaporated to provide 1.95 g (92%) 4-benzoyl-3,5-dichorobenzyl azide, IR (neat): 2090, 1670 cm-1.

Workup

  1. temperaturewas refluxed 5 hours
  2. temperaturecooled
  3. customevaporated
  4. dissolutionThe residue was dissolved in diethyl ether
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f670c43fffdc4d11ba0821f081d15740
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

Loading…