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Eelectrosynthesis of benzothiazole derivatives via C–H thiolation

Reza AhdenovChemistry and Chemical Engineering Research Center of Iran (CCERCI) , 14335-186 , Tehran , IranAli A. MohammadiDepartment of Organic Chemistry, Chemistry and Chemical Engineering Research Center of Iran (CCERCI) , 14335-186 , Tehran , IranSomayeh MakaremDepartment of Chemistry, Karaj Branch, Islamic Azad University , Karaj , IranSalman TaheriChemistry and Chemical Engineering Research Center of Iran (CCERCI) , 14335-186 , Tehran , IranHoda MollabagherChemistry and Chemical Engineering Research Center of Iran (CCERCI) , 14335-186 , Tehran , Iran
2022en
ABI

Abstract

Abstract Benzothiazole derivatives are essential intermediates in synthesizing a wide variety of medical and pharmaceutical compounds, and there is a great demand for a simple and efficient method to synthesize benzothiazoles under mild reaction conditions. Organic electrosynthesis as an energy-efficient process represents an environmentally benign and safer method than traditional methods for organic synthesis. Herein, we present bromine-free and straightforward synthesis of 2-amino benzothiazole derivatives via the reaction of aniline derivatives and ammonium thiocyanate using electrosynthesis in the presence of sodium bromide both as an electrolyte and as a brominating agent at room temperature in isopropyl alcohol (i-PrOH) as a solvent. The reaction of ammonium thiocyanate via C–H thiolation routes, using various aniline derivatives, resulted in a simple, green, and bromine-free synthesis of 2-amino benzothiazole in moderate to good yields under mild reaction conditions. Riluzole drug can be produced using the same procedure in moderate yields.

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