Phase Transfer Catalyzed Preparation of 4-Methylbenzenesulfonyl Imidazole for Regioselective Synthesis of Mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin

https://doi.org/10.22146/ijc.70252

I Wayan Muderawan(1*), I Wayan Mudianta(2), Made Kurnia Wiastuti Giri(3)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Ganesha University of Education, Singaraja 81117, Bali, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Ganesha University of Education, Singaraja 81117, Bali, Indonesia
(3) Study Program of Medicine, Faculty of Medicine, Ganesha University of Education, Singaraja 81117, Bali, Indonesia
(*) Corresponding Author

Abstract


The preparation of 4-methylbenzenesulfonyl imidazole by using triethylamine as an effective phase‐transfer catalyst (PTC) under mild biphasic conditions has been studied intensively. The method can be used for large-scale preparation with high purity and high yield of 4-methylbenzene-sulfonyl imidazole. The result in 4-methylbenzenesulfonyl imidazole has been successfully applied for the regioselective synthesis of mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin in an aqueous medium. This synthetic methodology concept, together with the synthetic versatility of PTC, provides a general and reliable general strategy for the practical and industrial regioselective synthesis of highly valuable mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin as a key intermediate for the single functional isomer mono-substituted cyclodextrin derivatives. As characterized by FTIR, NMR and mass spectrometry, mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin was obtained in high purity.

Keywords


phase transfer catalysis; 4-methylbenzene-sulfonyl imidazole; regioselective synthesis; mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin

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DOI: https://doi.org/10.22146/ijc.70252

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