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An improved method for the preparation of alkyl/arylurea derivatives using chlorocarbonylsulfenyl chloride as carbonylating agent

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Abstract

A convenient procedure has been developed for preparation of amine-substituted or monomethylamine-substituted alkyl/arylurea derivatives. The method comprises two steps—reaction of an alkyl/aryl amine with chlorocarbonylsulfenyl chloride in a non-polar solvent to produce an alkyl/arylcarbonylsulfenyl chloride, then reaction of this alkyl/arylcarbonylsulfenyl chloride with ammonia or monomethylamine in a two-phase reaction with a phase-transfer catalyst, to produce the corresponding alkyl/aryl-substituted urea.

Graphical Abstract

R 1 , R 2 : H, methyl, ethyl, propyl, butyl, benzyl, cyclohexyl; R 3 : H, methyl. A simple, one-pot, rapid, efficient, cost-effective, non-phosgene route for synthesis of alkyl/arylurea derivatives starting with the corresponding alkyl/aryl amine and chlorocarbonylsulfenyl chloride.

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Acknowledgments

The authors gratefully acknowledge the Center for Biomedical Magnetic Resonance (CBMR; SGPGIMS), Lucknow, for NMR spectra, and the Central Drug Research Institute (CDRI), Lucknow, for mass spectra. One of the authors (K. Adeppa) wishes to convey his grateful feelings of gratitude to India Pesticides Ltd, Lucknow, India, for providing all laboratory facilities and financial support, which made it possible to complete this work successfully.

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Authors and Affiliations

  1. Sri Venkateswara University, Tirupathi, Andhra Pradesh, India

    D. M. Manidhar, K. Uma Maheswara Rao, C. Suresh Reddy & Ch. Syamasunder

  2. Gautam Buddh Technical University, Lucknow, 226021, Uttar Pradesh, India

    K. Adeppa

  3. Indian Institute of Information Technology, Jhalwa Campus, Allahabad, 211002, Uttar Pradesh, India

    Krishna Misra

  4. R&D Centre, India Pesticides Limited, Lucknow, 226004, India

    K. Adeppa

Authors
  1. D. M. Manidhar
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  2. K. Uma Maheswara Rao
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  3. C. Suresh Reddy
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  4. Ch. Syamasunder
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  5. K. Adeppa
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  6. Krishna Misra
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Corresponding author

Correspondence to K. Adeppa.

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Manidhar, D.M., Uma Maheswara Rao, K., Suresh Reddy, C. et al. An improved method for the preparation of alkyl/arylurea derivatives using chlorocarbonylsulfenyl chloride as carbonylating agent. Res Chem Intermed 38, 2479–2489 (2012). https://doi.org/10.1007/s11164-012-0563-4

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  • DOI: https://doi.org/10.1007/s11164-012-0563-4

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