Methanesulfonic Acid → 5-(4-butoxyphenyl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a slurry of 1-(4-n-butyloxybenzoyl)thiosemicarbazide (20 g) in toluene (213.3 ml) at 40° C., was added dropwise over 30 minutes, methanesulfonic acid (6.92 ml). The mixture was stirred under refluxing for 12 hours. After cooling to 10° C., the sulfonate salt was filtered and dried. The salt was placed in water, the solution was adjusted to pH 9 with 1N sodium hydroxide and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 2-amino-5-(4-n-butyloxyphenyl)-1,3,4-thiadiazole (4.314 g).

Provenance & Evidence