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Synthesis 2007(12): 1819-1822  
DOI: 10.1055/s-2007-983715
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aromatic Aminosulfonic Acid Nitroamides

Kazimierz Minksztym*
Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland
Fax: +48(61)8658008; e-Mail: kmink@amu.edu.pl;
Further Information

Publication History

Received 21 February 2007
Publication Date:
08 June 2007 (online)

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Abstract

Nitration of aromatic aminosulfonic acid primary amides to furnish the corresponding sulfononitroamides has been described for the first time. The conditions of nitration applied ensure chemoselective mononitration and prevent decomposition of the product. Synthesis of dabsyl nitroamide sodium salt, as a potential β-amyloid aggregation inhibitor is also reported.

Key words

sulfonamides - nitration - amines - arenes - azo compounds

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16

In the modified procedure for the isolation of 2i, the reaction mixture after pouring onto ice was extracted with EtOAc (4 × 15 mL). The combined extracts were dried (MgSO4) and evaporated. The residue was chromatographed (silica gel, a hexane-EtOAc gradient solvent from 10:1 to 1:1) to give 2i followed by recovered 1i. Analytical data of the product 2i (mp, R f , 1H and 13C NMR) were consistent with a commercial sample of 2,6-dichloro-4-nitroaniline.