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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.8K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Solvents01:12

Solvents

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A solvent is a substance, most often a liquid, that can dissolve other substances. Here, the substance being dissolved is called a solute. When a solvent and a solute combine, they form a solution - a homogenous mixture of both the solvent and the solute. Water is a universal biological solvent. Its polar structure allows it to dissolve many other polar compounds. The ability of water to dissolve is governed by a balance between water molecules binding to each other and binding to the solute.
A...
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Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.3K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
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Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis.

Maristella Simone1, Mara Pulpito1, Filippo Maria Perna1

  • 1Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari "Aldo Moro", Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, Bari, I-70125, Italy.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 22, 2024
PubMed
Summary

This study introduces a green synthesis for sulfonamides using choline chloride-based deep eutectic solvents. This sustainable method offers high yields at ambient temperature, demonstrating its practicality for pharmaceutical intermediates.

Keywords:
AminesDeep eutectic solventsSulfonamidesSulfonyl chloridesSustainable chemistry

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Area of Science:

  • Green Chemistry
  • Organic Synthesis
  • Solvent Engineering

Background:

  • Sulfonamides are crucial in pharmaceuticals.
  • Traditional synthesis methods often involve harsh conditions and hazardous reagents.
  • Developing sustainable and efficient synthetic protocols is essential.

Purpose of the Study:

  • To develop a sustainable and scalable protocol for synthesizing functionalized sulfonamides.
  • To utilize environmentally responsible and reusable deep eutectic solvents (DESs).
  • To demonstrate the protocol's applicability in synthesizing pharmaceutical intermediates.

Main Methods:

  • Employing choline chloride (ChCl)-based DESs, specifically ChCl/glycerol and ChCl/urea mixtures.
  • Conducting reactions between amines and sulfonyl chlorides under aerobic conditions at ambient temperature.
  • Utilizing quantitative metrics like E-factor and EcoScale to assess eco-friendliness.

Main Results:

  • Achieved high yields (up to 97%) for various functionalized sulfonamides.
  • Demonstrated successful synthesis within 2-12 hours under mild conditions.
  • Successfully synthesized an FFA4 agonist and a precursor for the anti-Alzheimer drug BMS-299897.
  • Showcased product isolation via simple extraction or filtration after decantation.

Conclusions:

  • Choline chloride-based DESs provide a sustainable and efficient medium for sulfonamide synthesis.
  • The protocol is scalable, environmentally friendly, and practical for synthesizing valuable compounds.
  • The developed method offers a greener alternative to traditional sulfonamide synthesis routes.