A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

Nathalie Saraiva Rosa, Thomas Glachet, Quentin Ibert, Jean-François Lohier, Xavier Franck, Vincent Reboul*

*Normandie Univ, ENSICAEN, UNICAEN, CNRS, LCMT, 14000 Caen, France, Email: vincent.reboulensicaen.fr

N. S. Rosa, T. Glachet, Q. Ibert, J.-F. Lohier, X. Franck, V. Reboul, Synthesis, 2020, 52, 2099-2105.

DOI: 10.1055/s-0040-1707103

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Abstract

A direct and convenient reaction of primary amides with phenyliodine diacetate in the presence of an ammonia source (NH₃ or ammonium carbamate) provides N-substituted ureas. This transformation involves a nucleophilic addition of ammonia to an isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.

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Key Words

amides, ureas, PIDA, Hofmann rearrangement, isocyanates

ID: J66-Y2020