Potassium azide → 3,5-Dichloro-4-(4-chlorobenzoyl)benzyl azide

HRID 280652Notes

Reaction equation

HRID 280652 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[C:15]([Cl:16])=[CH:14][C:11]([CH2:12]Br)=[CH:10][C:9]=2[Cl:17])=[O:7])=[CH:4][CH:3]=1.[N-:20]=[N+:21]=[N-:22].[K+]>C(O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[C:15]([Cl:16])=[CH:14][C:11]([CH2:12][N:20]=[N+:21]=[N-:22])=[CH:10][C:9]=2[Cl:17])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10290740Potassium azideHCID 136496564-(4-Chlorobenzoyl)-3,5-dichlorobenzyl bromide

Product 1

HCID 136496623,5-Dichloro-4-(4-chlorobenzoyl)benzyl azideYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl bromide (3.2 g, 8.5 mmol) and potassium azide (1.3 g, 16 mmol) in ethanol (32 ml) was refluxed 5 hours, cooled, and filtered. The precipitate was washed once with ethanol and the combined filtrate and wash were evaporated under vacuum. The residue was triturated with diethyl ether (50 ml) and filtered. The filtrate was evaporated under vacuum to provide 2.92 g (100%) of 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl azide, m.p. 50°-55° C.

Workup

  1. temperaturewas refluxed 5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe precipitate was washed once with ethanol
  5. washthe combined filtrate and wash
  6. customwere evaporated under vacuum
  7. customThe residue was triturated with diethyl ether (50 ml)
  8. filtrationfiltered
  9. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-d349e108594544a898b47cc88d46c300
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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