Methyl iodide → 3-Methyl-5-[2-[(phenylmethyl)thio]phenyl]-1,3,4-oxadiazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2.9 g of potassium t-butoxide in 60 ml of DMF under a N2 atmosphere was added portionwise 7 g of the product of Example 1 while maintaining the reaction temperature at 25°-30° C. with an ice-water bath. After stirring at 25° C. for 1 hour, 7 g of methyl iodide was added dropwise to cause an exotherm to 37° C. The suspension was heated at 40°-60° C. for 5 hours, then cooled to 25° and poured onto excess ice-water to yield a precipitate. The suspension was filtered, and the isolated solid was dissolved in tetrahydrofuran and dried over MgSO4. The isolated solid was passed through a silica gel column with methylene chloride and, after evaporation of the first eluant, 5 g of the subject compound was obtained; m.p. 137°-140° C.

Provenance & Evidence