Affiliation:
1. Jilin Institute of Chemical Technology , Jilin 132022, China
2. Jilin University, College of Chemistry , Changchun 130021, China
Abstract
Abstract
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.
Subject
General Chemical Engineering,General Chemistry,Biotechnology
Reference17 articles.
1. 1. Gold, R.E., Bestman, H. & Haden, E. (2008). Patent No. 20110105320 A1. Washington, D.C.: U.S. Patent and Trademark Offi ce.
2. 2. Edwards, S.G. & Godley, N.P. (2010). Reduction of Fusarium head blight and deoxynivalenol in wheat with early fungicide applications of prothioconazole. Food Addit. Contam. 27(5), 629-635. DOI: 10.1080/19440040903515942.
3. 3. Xavier, S.A., Canteri, M.G. & Barros, D. (2013). Sensitivity of Corynespora cassiicola from soybean to carbendazim and prothioconazole. Trop. Plant Pathol. 38(5), 431-435. DOI: 10.1590/S1982-56762013005000020.
4. 4. Schisler, D.A. & Boehm, M.J. (2012). U.S. Patent No. 8,241,889. Washington, D.C.: U.S. Patent and Trademark Offi ce.
5. 5. Liu, M., Liu, H. & Li, P.R. (2003). Synthesis of 3-mercapto-4-oxopentyl acetate. Appl. Chem. Ind. 32(6), 53-54. DOI: 10.16581/j.cnki.issn1671-3206.2003.06.021.
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