Potassium azide → 4-(4-Chlorobenzoyl)-3-chlorobenzyl azide

HRID 280640Notes

Reaction equation

HRID 280640 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][C:9]=2[Cl:16])=[O:7])=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[K+]>C(O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][N:19]=[N+:20]=[N-:21])=[CH:10][C:9]=2[Cl:16])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10290740Potassium azideHCID 136496544-(4-Chlorobenzoyl)-3-chlorobenzyl bromide

Product 1

HCID 136496614-(4-Chlorobenzoyl)-3-chlorobenzyl azideYield 106.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of 4-(4-chlorobenzoyl)-3-chlorobenzyl bromide (1.60 g, 4.65 mmol) and potassium azide (0.715 g, 8.81 mmol) in ethanol (15 ml) was refluxed 5 hours, cooled to ambient temperature, and stirred 16 hours. The solids were filtered and washed twice with ethanol. The combined filtrate and washes were evaporated under vacuum, diluted with diethyl ether (40 ml), filtered, and evaporated under vacuum to provide 1.51 g (106% of theory) of 4-(4-chlorobenzoyl)-3-chlorobenzyl azide, m.p. 33°-33.5° C., suitable for subsequent reaction.

Workup

  1. temperaturewas refluxed 5 hours
  2. filtrationThe solids were filtered
  3. washwashed twice with ethanol
  4. customThe combined filtrate and washes were evaporated under vacuum
  5. additiondiluted with diethyl ether (40 ml)
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-ee83f3216d8e4f2f9e9b60dabba91e4f
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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