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

HRID 2374147Notes

Reaction equation

HRID 2374147 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:10][NH2:11])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14](OC)(OC)(OC)[CH3:15]>>[CH3:14][C:15]1[O:9][C:8]([C:7]2[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10][N:11]=1

Participants

3

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 3693744Benzoic acid, 4-nitro-, hydrazide

Product 1

HCID 5404162-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole

Procedure

4-Nitro-benzoic acid hydrazide (1.0 g, 5.6 mmol) was heated to reflux in trimethyl orthoacetate for 4 days. After cooling to RT, the mixture was triturated with hexanes and the title compound collected by filtration (0.93 g). MS (ESI+) for m/z 206 (M+H)+.

Workup

  1. customthe mixture was triturated with hexanes
  2. filtrationthe title compound collected by filtration (0.93 g)

Sources & evidence

ORD record
ord-86c7c7543ed843c9830b697803f89bd2
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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