2-Methoxybenzoic acid → 2-(2-Methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole

HRID 2421094Notes

Reaction equation

HRID 2421094 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:15][NH2:16])=[O:14].[CH3:17][O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=O>>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]1[O:14][C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:15][N:16]=1

Participants

3

Reactant 2

HCID 113702-Methoxybenzoic acidHCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazide

Product 1

HCID 167225352-(2-Methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazoleYield 55%

Procedure

As described for example 2, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (200 mg, 0.92 mmol) was converted using 2-methoxybenzoic acid instead of o-toluic acid to the title compound (SiO2, heptane:ethyl acetate 95:5 to 50:50, 170 mg, 55%) which was obtained as a white foam. MS: m/e=334.0 [M+H]+.

Sources & evidence

ORD record
ord-86abc8041b264d60a3322ad71b1eb4e5
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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