HCID 14835675, compound → HCID 14835676, compound

Reaction equation

[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:9][NH2:10])=[O:8].[CH:16]([O-])([O-])OC>>[CH3:15][O:14][CH:3]([O:2][CH3:1])[C:4]1[CH:5]=[C:6]([C:7]2[O:8][CH:16]=[N:10][N:9]=2)[CH:11]=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 14835675HCID 14835675, compound

HCID 53629101Methylorthoformate

Product 1

HCID 14835676HCID 14835676, compoundYield 61.4%

Procedure

2.1 g of 3-dimethoxymethylbenzhydrazide and 12.7 g of methyl orthoformate were reacted at atmospheric pressure for 24 hours while distilling off the methanol formed. Excessive methyl orthoformate was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=3/1) to obtain 1.35 g of colorless oily 2-(3-dimethoxymethylphenyl)-1,3,4-oxadiazole.

Workup

distillationwhile distilling off the methanol
customformed
customExcessive methyl orthoformate was removed by distillation under reduced pressure
customThe residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-4d560382b83a44feb0a329157b3c91ab
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948796

Reaction notes

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