2,5-dibromo-N'-[4-(octyloxy)benzoyl]benzohydrazide → 2-(2,5-Dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole

HRID 458490

Reaction equation

HRID 458490 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:3]=1[C:4]([NH:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][CH:10]=1)=O>P(Cl)(Cl)(Cl)=O>[Br:1][C:2]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:3]=1[C:4]1[O:24][C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][CH:10]=2)=[N:7][N:6]=1

Participants

3

Reactant 1

HCID 219821022,5-dibromo-N'-[4-(octyloxy)benzoyl]benzohydrazide

Product 1

HCID 219820732-(2,5-Dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazoleYield 89%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

A mixture of 2,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (39.1 g, 0.0743 mol) and phosphorus oxychloride (203 mL) was refluxed for 8 hrs. Unreacted phosphorus oxychloride was distilled off and the residue poured onto crushed ice. The precipitated solid was collected by filtration and re-crystallized from EtOH/water to give 33.6 g (89% yield) 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]1,3,4-oxadiazole.

Workup

  1. temperaturewas refluxed for 8 hrs
  2. distillationwas distilled off
  3. additionthe residue poured
  4. customonto crushed ice
  5. filtrationThe precipitated solid was collected by filtration
  6. customre-crystallized from EtOH/water

Sources & evidence

ORD record
ord-155e2d177b64459fbe2de377a1f1cb55
Source dataset
uspto-grants-2007_03
Patent number
US07192657B2

Linked notes

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