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DOI: 10.1055/s-0028-1083564
Efficient Removal of Amines Using Polymer-Supported Cyclic Anhydride
Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro WatanabeUniversity of Nottingham and Merck Chemicals Ltd., Nottingham, UK
A Macroporous Polymer-Supported Cyclic Anhydride for Efficient Sequestration of Amines
Tetrahedron Lett. 2008, 49: 6160-6162
Publication History
Publication Date:
20 November 2008 (online)
Key words
polymer-supported reagents - poly(methacrylic anhydride) - electrophilic scavengers - parallel synthesis
Significance
The simple and efficient removal of primary and secondary amines from organic solutions was realized by a novel macroporous polymer-supported acid anhydride 1. The amine-scavenging ability of the anhydride resin 1 was examined for small-scale parallel synthesis of ureas. Thus, the reaction of allylisocyanate 2 with an excess amount of amines 3 was carried out at room temperature, and the resulting reaction mixture was treated with the scavenger 1 to afford the corresponding ureas 4 in 47-79% yield with high purity.
Comment
The loading of macroporous polymer-supported anhydride 1 is 5.0-6.7 mmol/g. The polymer 1 is commercially available from Merck Chemicals Ltd. The percentage of scavenged amines was estimated using ¹H NMR spectroscopy.