4-Chlorobenzohydrazide → 2-(4-Chlorophenyl)-1,3,4-oxadiazole

HRID 1710018Notes

Reaction equation

HRID 1710018 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH:12](OCC)(OCC)OCC>>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:12]=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 108164-ChlorobenzohydrazideHCID 31214Ethyl orthoformate

Product 1

HCID 116007772-(4-Chlorophenyl)-1,3,4-oxadiazole

Procedure

A stirred solution of 8.1 grams (0.048 mole) of 4-chlorobenzoic acid hydrazide in 300 ml of triethyl orthoformate was heated under reflux for 16 hours. The excess triethyl orthoformate was removed by distillation and the residual solid was stirred with petroleum ether to yield 7.7 grams of 2-(4-chlorophenyl)-1,3,4-oxadiazole; m.p. 129° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe excess triethyl orthoformate was removed by distillation

Sources & evidence

ORD record
ord-d0b91243f74d48b094771a53d8a24f30
Source dataset
uspto-grants-1990_08
Patent number
US04952580

Reaction notes

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