Triethyl orthoacetate → 2-Methyl-5-(3-nitrophenyl)-1,3,4-oxadiazole

HRID 621468

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:9][NH2:10])=[O:8])([O-:3])=[O:2].[CH2:14](OC(OCC)(OCC)C)[CH3:15]>>[CH3:14][C:15]1[O:8][C:7]([C:6]2[CH:11]=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[N:9][N:10]=1

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 32914983-Nitrobenzohydrazide

Product 1

HCID 28063312-Methyl-5-(3-nitrophenyl)-1,3,4-oxadiazole

Procedure

3-Nitrobenzoic acid, hydrazide, 24.5 g, (Chemical Abstracts, Vol. 102, 148507r (1983)) and 1,1,1-triethoxyethane are refluxed overnight. The mixture is cooled, filtered, and washed with hexane to give 21.9 g of 2-methyl-5-(3-nitrophenyl)-1,3,4-oxadiazole after recrystallization from 2-propanol; mp 154°-156° C.

Workup

temperatureThe mixture is cooled
filtrationfiltered
washwashed with hexane

Sources & evidence

ORD record: ord-98704e72f22c4bcb92d71e2e7f36b26c
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04824843

Linked notes

Loading…