Sodium Azide → 4-(2-Naphthoyl)-3,5-dichlorobenzyl azide

HRID 1650191Notes

Reaction equation

HRID 1650191 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([C:13]1[C:20]([Cl:21])=[CH:19][C:16]([CH2:17]Br)=[CH:15][C:14]=1[Cl:22])=[O:12].[N-:23]=[N+:24]=[N-:25].[Na+]>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([C:13]1[C:20]([Cl:21])=[CH:19][C:16]([CH2:17][N:23]=[N+:24]=[N-:25])=[CH:15][C:14]=1[Cl:22])=[O:12]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 147000274-(2-Naphthoyl)-3,5-dichlorobenzyl bromide

Product 1

HCID 147000284-(2-Naphthoyl)-3,5-dichlorobenzyl azideYield 103.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-(2-naphthoyl)-3,5-dichlorobenzyl bromide (0.633 g, 1.61 mmol) and sodium azide (0.245 g, 3.77 mmol) in 10 ml of ethanol was heated at reflux for 3 hours. The reaction mixture was filtered and the precipitate rinsed with ethanol. The filtrate was concentrated and the residue redissolved in ether. The resulting precipitate was collected and washed thoroughly with ether. Concentration afforded 0.594 g of an oil which slowly crystallized. The crude azide was used in the next step without any further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate rinsed with ethanol
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue redissolved in ether
  7. customThe resulting precipitate was collected
  8. washwashed thoroughly with ether
  9. concentrationConcentration

Sources & evidence

ORD record
ord-65223d951e464d58a32c339488d46a80
Source dataset
uspto-grants-1990_05
Patent number
US04923885

Reaction notes

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