<abstract xmlns="http://www.w3.org/1999/xhtml"> 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.</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.

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

Polish Journal of Chemical Technology

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

A simple and efficient method to prepare 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)ethan-1-one via nucleophilic substitution of...

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

Publié en ligne: 11 mai 2017

Pages: 41 - 47

DOI: https://doi.org/10.1515/pjct-2017-0006

Mots clés
prothioconazole, 1,2,4-triazole, N-alkylation reaction

© by Chuanbo Dai

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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

Publié en ligne: 11 mai 2017

Pages: 41 - 47

DOI: https://doi.org/10.1515/pjct-2017-0006

Mots clésprothioconazole, 1,2,4-triazole, N-alkylation reaction

© by Chuanbo Dai

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Mots clés
prothioconazole, 1,2,4-triazole, N-alkylation reaction