1-Propanol → 5-(4-(benzyloxy)phenyl)-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-one

HRID 2372811Notes

Reaction equation

HRID 2372811 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](#[N:22])[CH:20]=[CH2:21].[CH2:23]([OH:26])CC>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:23](=[O:26])[N:16]([CH2:21][CH2:20][C:19]#[N:22])[N:15]=2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 7855Acrylonitrile2×HCID 15264864-(Benzyloxy)benzohydrazide

Product 1

HCID 30358125-(4-(benzyloxy)phenyl)-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-oneYield 88%

Procedure

To a solution of 100 mmoles of (4-benzyloxy benzoyl) hydrazine in 200 ml of 1-propanol, 100 mmoles of acrylonitrile are added and the mixture is heated for 24 hours at reflux. Then 50 mmoles of acrylonitrile are added and the heating is continued at reflux for 24 hours. After cooling, the product is filtered and crystallized in a water-ethanol mixture and 26 g (yield: 88%) of the expected product were obtained.

Workup

  1. temperaturethe mixture is heated for 24 hours
  2. temperatureat reflux
  3. temperatureat reflux for 24 hours
  4. temperatureAfter cooling
  5. filtrationthe product is filtered
  6. customcrystallized in a water-ethanol mixture

Sources & evidence

ORD record
ord-8f0ceb9136ad43e1a08d0502b1d140ba
Source dataset
uspto-grants-1992_03
Patent number
US05100910

Reaction notes

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