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Synthesis of 2-(o-Hydroxyphenyl)-Benzothiazole and of 2-(o-Hydroxyphenyl)-Benzothiazoline

Journal Article · · Journal of Organic Chemistry
DOI:https://doi.org/10.1021/jo01132a009· OSTI ID:4378032

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).

Research Organization:
Univ. of Pittsburgh, PA (United States)
Sponsoring Organization:
US Atomic Energy Commission (AEC)
NSA Number:
NSA-06-006581
OSTI ID:
4378032
Report Number(s):
NYO--3767
Journal Information:
Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 4 Vol. 18; ISSN 0022-3263
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English