ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Reaction of 2-benzothiazolythioethanoic acid with phthalic-anhydride under conditions of Gabriel modification of Perkin synthesis

M. Lácová

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, CS-842 15 Bratislava

Abstract: In addition to the anticipated 3-(2-benzothiazolylthiomethylene)phthalide four more compounds resulted from the reaction of 2-benzothiazolyl- thioethanoic acid with phthalic anhydride under conditions of Gabriel modifi- cation of Perkin synthesis. These four compounds were identified as (Z,Z)-, (E,Z)-3,3'-thio-bis(methylenephthalide), l-(2-benzothiazolyloxy)-l-inden-3- -one, and dibenzothiazolyl disulfide. The starting compounds did not react in the presence of acetic anhydride, since 2-benzothiazolylthioethanoic acid was preferentially acetylated to yield 4-methylthiazo[2,3-b]benzothiazolium 5-car- boxylate by an intramolecular condensation.

Full paper in Portable Document Format: 401a95.pdf

Chemical Papers 40 (1) 95–102 (1986)