The synthesis of the title compound has been reported by two related procedures. Cyclization of phenacyl N-(4-fluorophenyl)carbamate (I) in boiling HOAc gave rise to oxazolone (II). Chlorosulfonation of (II), followed by treatment of the resulting sulfonyl chloride (III) with ammonia, yielded the title sulfonamide.
In an alternative procedure, sodium 4-acetylbenzenesulfonate (IV) was refluxed with POCl3 and subsequently treated with dibenzylamine to afford sulfonamide (V). Bromination of (V) in chloroform yielded the bromo ketone (VI), which was hydrolyzed to phenacyl alcohol (VII) by treatment with ethanolic betaine, followed by aqueous NaHCO3. Addition of 4-fluorophenyl isocyanate (VIII) to (VII) and then cyclization in refluxing HOAc yielded the oxazolone (IX). Final debenzylation was achieved with concentrated H2SO4 to give the target sulfonamide.