Synthesis and Characterization of 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)ethan-1-one

• Autorzy: Ji H. , Niu Y. , Liu D. , Wang W. , Dai C.

Identyfikatory

DOI

10.1515/pjct-2017-0006

• Języki publikacji: EN

Abstrakty

EN

A simple and efficient method to prepare 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)ethan-1-one via nucleophilic substitution of 2-chloro-1-(1-chlorocyclopropyl)ethanone and 1,2,4-triazole is described. The title compound is the key intermediate required for the synthesis of prothioconazole, a promising agricultural fungicide. By exploring changes in the reaction time, temperature, ratio of starting reagents, acid binding agent, and the nature of phase transfer catalyst, the reaction conditions could be optimized to afford the desired N-alkylated material in near-quantitative yield. The ultimate yield of the product after recrystallization was 93%, with a purity of 99% based on its characterization by Gas Chromatography-Mass Spectrometer (GC-MS), Fourier Transform infrared spectroscopy (IR), Proton Magnetic Resonance (¹H NMR), and Carbon-13 Nuclear Magnetic Resonance (¹³C NMR). The synthetic process is suitable for industrial application, with the advantages of high yield and facile preparation under mild operating conditions.

Słowa kluczowe

EN

prothioconazole; 1,2,4-triazole; N-alkylation reaction

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2017
• Tom: Vol. 19, nr 1
• Strony: 41--47
• Opis fizyczny: Bibliogr. 17 poz., rys., tab.

Twórcy

autor

Ji H.

• Jilin Institute of Chemical Technology, Jilin 132022, China

autor

Niu Y.

• Jilin University, College of Chemistry, Changchun 130021, China

autor

Liu D.

• Jilin Institute of Chemical Technology, Jilin 132022, China

autor

Wang W.

• Jilin Institute of Chemical Technology, Jilin 132022, China

autor

Dai C.

• Jilin Institute of Chemical Technology, Jilin 132022, China

Bibliografia

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Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).