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A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

Nathalie Saraiva Rosa 1 Thomas Glachet 1 Quentin Ibert 1 Jean-François Lohier 1 Xavier Franck 2 Vincent Reboul 1
1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.
Keywords : Isocyanates Hofmann rearrangement Hypervalent iodine Amides Ureas
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02569464
Contributor : Madeleine Roux-Merlin <>
Submitted on : Monday, May 11, 2020 - 1:13:24 PM
Last modification on : Wednesday, November 18, 2020 - 3:29:34 AM

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INC-CNRS | INSA-ROUEN | UNIROUEN | ENSICAEN | LCMT | COBRA | INSA-GROUPE | UNICAEN | CNRS | UNILEHAVRE | COMUE-NORMANDIE

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Nathalie Saraiva Rosa, Thomas Glachet, Quentin Ibert, Jean-François Lohier, Xavier Franck, et al.. A Straightforward Synthesis of N-Substituted Ureas from Primary Amides. SYNTHESIS, Georg Thieme Verlag, 2020, (in press). ⟨10.1055/s-0040-1707103⟩. ⟨hal-02569464⟩

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