5-Methyl-3-phenyl-4-isoxazolecarbohydrazide → 2-(4-Fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole

HRID 1983104

Reaction equation

HRID 1983104 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].[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=O)=[C:20]([O:27][CH3:28])[CH:19]=1>>[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]2[O:14][C:13]([C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])=[N:15][N:16]=2)=[C:20]([O:27][CH3:28])[CH:19]=1

Participants

3

Reactant 2

HCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazideHCID 27745454-Fluoro-2-methoxybenzoic acid

Product 1

HCID 167226452-(4-Fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazoleYield 49%

Procedure

As described for example 2, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (2.00 g, 9.12 mmol) was converted using 4-fluoro-2-methoxy-benzoic acid instead of o-toluic acid to the title compound (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20, 1.59 g, 49%) which was obtained as a white solid. MS: m/e=352.3 [M+H]+.

Sources & evidence

ORD record
ord-ada36cb5d0974f17a38517d07cf24731
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Linked notes

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