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Conversion of 4-substituted benzo-2,1,3-thiadiazoles to 5-chloro-4,7-dioxobenzo-2,1,3-thiadiazole by action of hydrogen peroxide and hydrochloric acid

✍ Scribed by I. A. Belen'kaya; G. P. Krokhina; S. A. Sirik; S. A. Andronati

Book ID: 104781951
Publisher: Springer US
Year: 1988
Tongue: English
Weight: 356 KB
Volume: 24
Category: Article
ISSN: 0009-3122
DOI: 10.1007/bf00475579

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✦ Synopsis

Under the influence of hydrogen peroxide and hydrochloric acid in acetonitrile 4-substituted benzo-2,1,3-thiadiazoles form 5-chloro-4,7-dioxobenzo-2,1,3thiadiazole. 4-Alkoxy-and 4-[(alkoxycarbonyl)methoxy]benzo-2,1,3-thiadiazoles give, in addition, the corresponding 5,7-dichloro derivatives.

5-Chloro-4,7-dioxobenzo-2,1,3-thiadiazole (II) is formed in ~40% yield in the oxidation of 4ohydroxybenzo-2,1,3-thiadiazole (I) with 30% hydrogen peroxide in concentrated hydrochloric acid [I]. Since II has herbicidal activity and, in a dose of 5-10 kg/ha, suppresses the development of a green mass on garden radishes, flax, and beets by 87-100%,* it seemed expedient to examine other possibilities for obtaining quinone II and, for this purpose, to study the transformations of various 4-substituted benzo-2,1,3-thiadiazoles under the conditions indicated above.

Quinone II was isolated in 61%, 41%, and 54% yields, respectively~ in the oxidation of 4-amino-, 4-methylamino-~ and 4-acetoxybenzo-2,1,3-thiadiazole (III-V). An author's certificate was obtained for a method for obtaining quinone II from amine III [2].

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