Methyl iodide → 3-Methyl-5-[2-[(phenylmethyl)thio]phenyl]-1,3,4-oxadiazol-2(3H)-one
Reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH2:13][S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[O:25][C:24](=[O:26])[NH:23][N:22]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI>CN(C=O)C>[CH3:1][N:23]1[N:22]=[C:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14][CH2:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:25][C:24]1=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
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.
Workup
- temperaturewhile maintaining the reaction temperature at 25°-30° C. with an ice-water bath
- customto 37° C
- temperatureThe suspension was heated at 40°-60° C. for 5 hours
- temperaturecooled to 25°
- customto yield a precipitate
- filtrationThe suspension was filtered
- dissolutionthe isolated solid was dissolved in tetrahydrofuran
- dry with materialdried over MgSO4
- customafter evaporation of the first eluant
Sources & evidence
- ORD record
- ord-f815149f44a94dd88b40aae5c96a2d12
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04764205
Reaction notes
Loading…