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Procedures are described for the preparation of various bidentate and linear tetradentate benzimidazoles and benzothiazoles incorporating units such as pyridyl and thioether, and for the preparation of certain thioether dicarboxylic acids precursory to them. Condensations of ortho‐functinal anilines with carboxylic acids were carried out in polyphosphoric acid or refluxing HCl solution. Syntheses are reported for: [HO2C(CH2)2S(CH2)2]2X (X = O, S), 1,9‐bis(benzimidazol‐2‐yl)‐2,5,8‐trithianonane, 1,11‐bis(N‐methylbenzimidazol‐2‐yl)‐3,6,9‐trithiaundecane, 1,11‐bis(2‐benzimidazol‐2‐yl)‐6‐oxo‐3,9‐dithiaundecane, 2‐(2‐pyridyl)benzothiazole, 2,6‐bis(benzothiazol‐2‐yl)pyridine, 2‐(2‐pyridyl)‐N‐methylbenzimidazole, 2‐(2‐pyridylmethyl)benzimidazole and 2‐(N‐methyl‐2‐piperidyl)benzimidazole. The compounds were characterized, where appropriate, by their mass, uv and 1H‐nmr spectra.

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Procedures are described for the preparation of various bidentate and potentially tridentate chelating agents. These incorporate pyridyl, benzimidazole, imidazole or phenolic moieties. Phillips condensations of carboxylic acids with o‐phenylenediamines were carried out in 4 M hydrochloric acid. Syntheses are reported for 2, 6‐bis(N′‐methylimidazol‐2′‐ylthiomethyl)pyridine, 2, 6‐bis(benzimidazol‐2′‐ylthiomethyl)pyridine, 2‐(4′‐piperidyl)benzimidazole, 2‐(3′‐piperidyl)benzimidazole, 2‐(3‐N′‐methylpiperidyl)benziinidazole, 2‐(3‐N′‐methylpiperidyl)‐N‐methylbenzimidazole, 2‐(2′‐hydroxybenzyl)benzimidazole and 2‐(2′‐hydroxyben‐zyl)N‐methylbenzimidazole. The compounds were characterized where appropriate by their mass, uv, and 1H‐nmr spectra. 2‐(2′‐Hydroxybenzyl)benzimidazole hydrochloride acts as a gelling agent in aqueous solution.

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