Triethyl orthoacetate → 2-(5-Bromo-1-naphthyl)-5-methyl-1,3,4-oxadiazole

HRID 1276287Notes

Reaction equation

HRID 1276287 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([NH:14][NH2:15])=[O:13].[C:16](OCC)(OCC)(OCC)[CH3:17]>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]1[O:13][C:16]([CH3:17])=[N:15][N:14]=1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 221158865-Bromo-1-naphthohydrazide

Product 1

HCID 221158772-(5-Bromo-1-naphthyl)-5-methyl-1,3,4-oxadiazoleYield 88%

Procedure

5-Bromo-1-napthoic hydrazide (D2) (2.00 g, 7.5 mmol) was stirred at reflux under Ar in triethyl orthoacetate (20 ml) for 20 h. The mixture was cooled in ice, and the solid was filtered off, washed with petroleum ether (b.p. 60-80° C.), and dried in vacuo at 60° C., giving the title compound (1.92 g, 88%) as a light brown powder.

Workup

  1. temperatureThe mixture was cooled in ice
  2. filtrationthe solid was filtered off
  3. washwashed with petroleum ether (b.p. 60-80° C.)
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-7bd92942b1914e18b8fcc37edbaca74d
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Reaction notes

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