Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2024 Oct 1;30(55):e202402293.
doi: 10.1002/chem.202402293. Epub 2024 Sep 17.

Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis

Maristella Simone  1 , Mara Pulpito  1 , Filippo Maria Perna  1 , Vito Capriati  1 , Paola Vitale  1
Affiliations

Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis

Maristella Simone et al. Chemistry. .

Abstract

A sustainable and scalable protocol for synthesizing variously functionalized sulfonamides, from amines and sulfonyl chlorides, has been developed using environmentally responsible and reusable choline chloride (ChCl)-based deep eutectic solvents (DESs). In ChCl/glycerol (1 : 2 mol mol-1) and ChCl/urea (1 : 2 mol mol-1), these reactions yield up to 97 % under aerobic conditions at ambient temperature within 2-12 h. The practicality of the method is exemplified by the sustainable synthesis of an FFA4 agonist and a key building block en route to anti-Alzheimer drug BMS-299897. A subtle interplay of electronic effects and the solubility characteristics of the starting materials in the aforementioned DESs seem to be responsible for driving the reaction successfully over the hydrolysis of sulfonyl chlorides. The procedure's eco-friendliness is validated by quantitative metrics like the E-factor and the EcoScale, with products isolated by extraction or filtration after decantation.

Keywords: Amines; Deep eutectic solvents; Sulfonamides; Sulfonyl chlorides; Sustainable chemistry.

PubMed Disclaimer

References

    1. None
    1. E. E. Connor, Prim. Care Update Ob/Gyns. 1998, 5, 32–35;
    1. M. G. Perrone, L. Bleve, E. Santandrea, P. Vitale, M. Niso, A. Scilimati, ChemMedChem 2009, 4, 2080–2097;
    1. M. Bevilacqua, E. Magni, Drugs 1993, 46, 40–47;
    1. A. Scozzafava, T. Owa, A. Mastrolorenzo, C. T. Supuran, Curr. Med. Chem. 2003, 10, 925–953;