Sodium Azide → 3-(4-Chlorobenzoyl)-benzyl azide

HRID 280637Notes

Reaction equation

HRID 280637 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11]Br)=[O:7])=[CH:4][CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+]>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11][N:18]=[N+:19]=[N-:20])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 136496533-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 136496603-(4-Chlorobenzoyl)-benzyl azideYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-chlorobenzoyl)benzyl bromide (4.2 g, 13.6 mmol) and sodium azide (1.32 g, 20.3 mmol) in ethanol (40 ml) was refluxed for 5 hours, cooled to ambient temperature, and kept 16 hours. The mixture was filtered and the solids were washed twice with ethanol. The combined filtrate and washes were evaporated to dryness under vacuum and the residue was treated with diethyl ether and filtered. The filtrate was evaporated to dryness under vacuum and dried to provide 3.7 g (100%) of 3-(4-chlorobenzoyl)-benzyl azide, m.p. 43°-45° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe mixture was filtered
  3. washthe solids were washed twice with ethanol
  4. customThe combined filtrate and washes were evaporated to dryness under vacuum
  5. additionthe residue was treated with diethyl ether
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under vacuum
  8. customdried

Sources & evidence

ORD record
ord-797ab928d8754b319797ffa3ce390464
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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