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

HRID 34879Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:18][C:17](=[O:19])[NH:16][N:15]=1.CI>CN(C=O)C>[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:18][C:17](=[O:19])[N:16]([CH3:1])[N:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

temperaturewhile maintaining the reaction temperature at 10°-20° C. with external cooling
stirringAfter stirring at room temperature for 16 hours
filtrationfiltered
customThe residue was recrystallized from 2-propanol

Sources & evidence

ORD record: ord-2bdfaf3288b94c19b6debeb07bc4e2c0
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04764205

Reaction notes

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