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Synthesis of N-monosubstituted ureas in a mixture of choline chloride and aluminium nitrate as a simple, efficient, and selective process

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Abstract

The reaction involving benzyl alcohol or benzyl halide and urea, conducted within a mixture comprising choline chloride and aluminium nitrate ionic liquid as the solvent, leads to the synthesis of N-monosubstituted urea products. The reaction demonstrates notable to exceptional yields for various derivatives of benzyl alcohols and benzyl halides under the specified reaction conditions. When benzyl halides and benzyl alcohol undergo reactions with urea in the presence of the prepared ionic liquid, a sole selective pathway is observed, resulting in a considerable yield of N-monosubstituted urea products. This approach offers several advantages, including reaction selectivity, high product efficiency, facile separability of products, the environmentally benign nature of the solvent, and the omission of expensive and hazardous catalysts. These attributes underscore the significance of such pioneering reactions. Due to the markedly polar attributes and insolubility of the resulting products in water, facile separation from the reaction milieu is facilitated through the introduction of water into the reaction mixture. Consequently, this specific ionic liquid methodology provides an uncomplicated and selective avenue for the synthesis of compounds possessing noteworthy pharmaceutical and industrial utility.

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Data availability

The authors declare that the data supporting the findings of this study are available within the paper and its Supplementary Information files. Should any raw data files be needed in another format they are available from the corresponding author upon reasonable request.

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Acknowledgements

We are grateful to Tarbiat Modares University for financial support of this work.

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  1. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    Mohammadreza Jafari, Atefeh Darvishi & Akbar Heydari

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  1. Mohammadreza Jafari
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  2. Atefeh Darvishi
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  3. Akbar Heydari
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Correspondence to Akbar Heydari.

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Jafari, M., Darvishi, A. & Heydari, A. Synthesis of N-monosubstituted ureas in a mixture of choline chloride and aluminium nitrate as a simple, efficient, and selective process. Monatsh Chem 154, 1295–1306 (2023). https://doi.org/10.1007/s00706-023-03131-x

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