4-Bromobenzohydrazide → 2-(4-Bromophenyl)-5-methyl-1,3,4-oxadiazole

HRID 1003704

Reaction equation

HRID 1003704 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[C:12](OCC)(OCC)(OCC)[CH3:13]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][C:12]([CH3:13])=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222194-BromobenzohydrazideHCID 66221Triethyl orthoacetate

Product 1

HCID 5406932-(4-Bromophenyl)-5-methyl-1,3,4-oxadiazoleYield 87%

Procedure

A stirred suspension of 4-bromobenzoic hydrazide (4.0 g, 18.6 mmol) in triethyl orthoacetate (15 ml) was heated under reflux for 24 h. The reaction mixture was cooled and the precipitate filtered, washed with 60-80° C. petroleum ether (20 ml) and dried to give the title compound as a yellow solid (3.86 g, 87%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitate filtered
  5. washwashed with 60-80° C. petroleum ether (20 ml)
  6. customdried

Sources & evidence

ORD record
ord-77deb1aae56a4c75b9cfb0feaa4e0936
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Linked notes

Loading…