In the course of an investigation of the structure and behavior of organic chelating agents analogous to 8-hydroxyquinoline, it was decided to study the behavior of 2-(o-hydroxyphenyl)benzoxazole (I) and its sulfur analog, 2-(o-hydroxyphenyl)benzothiazole (II). This latter compound is described several places in the literature as being the product of the condensation of salicylaldehyde and o-aminobenzenethiol. Finally, our attempts to prepare II in this manner resulted in a product which was found to react with metals in a strikingly different manner than did the benzoxazole, I. This suggested to us the possibility that we had prepared 2-(o-hydroxyphenyl)benzothiazoline (III).
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Charles et al. (1953) studied this question.