2,5-Dimercaptoterephthalic acid was prepared by four routes to permit assessment of their relative merits for a bifunctional system and to permit confirmation of structures of useful intermediates through interconnections of the routes (Scheme I). The routes were: (I) conversion of the phenol to the , -bisthiocarbamate, rearrangement of this to the S,S-bisthiocarbamate, then saponification; (II) cleavage of 2,5-bisbenzyl thioether moieties of the terephthalate diester, then saponification; (III) reaction of potassium hydrosulfide with 2,5dibromoterephthalic acid; and (IV), route II but with the acid instead of the ester. 2-Mercaptoterephthalic acid was prepared by similar routes for the same reasons.Both the mono-and dimer capto acids reacted with aminoalkyl thiolsulfonates to give unsymmetrical aminoalkyl disulfides (Scheme II). Several products of Schemes I and II are of interest for further chemical studies and, particularly, for biological evaluation as antiradiation drugs, against histoplasmosis, or against schistosomiasis.
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