Hydrochloric Acid → 2-[4-(Benzyloxy)phenyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

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By the procedure of Example 4, Step C, p-(benzyloxy)phenylhydrazine [generated from the hydrochloride by partitioning between ether and 1N Na2CO3. The p-(benzyloxy)phenylhydrazine hydrochloride was prepared from the corresponding aniline according to H. Stroh and G. Westphal, Chem. Ber., 96, 184 (1963)] was reacted with ethyl N-carbethoxyvalerimidate (from Example 4, Step B). After work-up, the residue was purified by flash chromatography on silica gel to give a 9% yield of the desired compound, homogeneous by TLC in 19.1 CH2Cl2 /CH3OH; mass spectrum (FAB) m/e 324 (M+1)+.

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