Dimethylformamide → 5-(3-Chloro-4-cyclohexylphenyl)-3-(4-(chloromethyl)phenyl)-1,2,4-oxadiazole

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.27 mL, 0.0037 mol) and N,N-dimethylformamide (0.1 mL) are added to a stirred solution of {4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]phenyl}methanol (0.45 g, 0.0012 mol) in dichloromethane (10 mL) at 0° C. The reaction mixture is heated at 40-45° C. and is stirred at this temperature for 1 hr. It is then cooled to 0-5° C. temperature, treated with demineralized water (3 mL) and is neutralized with 4N sodium hydroxide solution at 0-5° C. to adjust the pH 8-9. Finally it is extracted with dichloromethane (2×10 mL) and the combined extract is dried over sodium sulfate. Removal of solvent under reduced pressure gives 5-(3-chloro-4-cyclohexylphenyl)-3-(4-chloromethylphenyl)-[1,2,4]-oxadiazole.

Provenance & Evidence