N,O-ditosylethanolamine as effective reagent for the synthesis of heterocyclic tertiary amine salts

ABSTRACT

During the synthesis of N-tosylaziridine, two unexpected products were isolated: 1-(2-(p-tolylsulfonamido)ethyl)pyridinium p-tolylsulfonate (3) and N,N,O-tri-(p-tolylsulfonyl)ethanolamine (3a). The structures of 3 and 3a were investigated in solid state by X-ray analysis. A new family of related salts was obtained using an efficient and facile one-pot synthesis consisting in the interaction between various nitrogen heterocycles and N,O-ditosylethanolamine.

GRAPHICAL ABSTRACT

KEYWORDS:

• Sulfonamide
• ethanolamines
• synthesis
• X-ray diffraction

Funding

This work is supported by the RFBR (12–03-00206-а) and by President Grant for Young Russian Scientists (MD-3634.2012.3). This work was supported in part by M.V. Lomonosov Moscow State University Program of Development.