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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 255828Generated: October 30, 2026

Methyl iodide → 5-(2-Hydroxyphenyl)-3-methyl-1,3,4-oxadiazol-2(3H)-one

https://huagongshe.com/reaction/255828

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantPotassium tert-butoxideHCID 23665647—
Reactanto-Hydroxyphenyl-1,3,4-oxadiazol-2-olHCID 135624284—
SolventDimethylformamideHCID 6228—
Product5-(2-Hydroxyphenyl)-3-methyl-1,3,4-oxadiazol-2(3H)-oneHCID 13562428571.1%

Reaction Conditions

Temperature25 °C

Reaction Steps

To a suspension of 3.8 g of potassium t-butoxide in 60 ml of dry DMF under a N2 atmosphere was added portionwise 6 g of the product of Example 10 while maintaining the reaction temperature at 10°-20° C. with external cooling. After stirring at 25° C. for one hour, 9.6 g of methyl iodide was added dropwise at 10°-20° C. with external cooling. After stirring at room temperature for 16 hours, the suspension was poured into excess ice-water and filtered. The residue was recrystallized from 2-propanol to yield 4.6 g of the subject compound; m.p. 160°-162° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04699647
Source datasetuspto-grants-1987_10
ORD IDord-789910e40051444c92969fdfd665323b
Source noteuspto-grants-1987_10