3-Substituted-4-amino-5-mercapto-1, 2, 4-triazole (3) was obtained in an excellent yield in a single step by the condensation of a well known drug norfloxacin having free carboxyl group (1) with thiocarbohydrazide (2). Various 3-Substituted-4-amino-5-mercapto-1, 2, 4-triazoloSchiff bases (4a1-a11) have been synthesized by the condensation of the mercapto triazole (3) with different aromatic aldehydes. The triazolo Schiff bases (4a1-a11) on heating with 2-Amino-7-chloro-6-fluorobenzothiazole in equimolar proportions yielded the required 3-Substitued-5-(2’-imino-7- chloro-6-fluorobenzothiazolyl) 1, 2, 4-triazolo Schiff bases (5a1-a11). The structures of newly synthesized compounds have been established on the basis of their spectral data and elemental analysis. Some selected compounds were screened for analgesic and anti-inflammatory activity. Some of the compounds exhibited encouraging results.