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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

3.0K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.0K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

10.3K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
10.3K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

3.0K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.0K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.3K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.3K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.5K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.3K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.3K

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Reactive deep eutectic solvents for EDC-mediated amide synthesis.

Debora Procopio1, Carlo Siciliano1, Maria Luisa Di Gioia1

  • 1Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036, Arcavacata of Rende, Italy. ml.digioia@unical.it.

Organic & Biomolecular Chemistry
|December 21, 2023
PubMed
Summary
This summary is machine-generated.

This study introduces a greener amide synthesis method using Reactive Deep Eutectic Solvents (RDESs). This sustainable approach avoids hazardous solvents and simplifies purification, advancing eco-friendly pharmaceutical production.

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Area of Science:

  • Green chemistry
  • Organic synthesis
  • Pharmaceutical manufacturing

Background:

  • Amide bond formation is crucial in pharmaceuticals, but traditional methods often lack sustainability.
  • Developing eco-friendly amide synthesis remains a significant challenge for the industry.

Purpose of the Study:

  • To develop a greener and more efficient method for amide synthesis.
  • To utilize Reactive Deep Eutectic Solvents (RDESs) as both reaction medium and reactants.

Main Methods:

  • Employing RDESs for amide bond formation, eliminating hazardous solvents.
  • Implementing a procedure for simple product recovery without chromatographic purification.
  • Applying the method to synthesize a key intermediate for atenolol.

Main Results:

  • The RDES method demonstrated high purity and efficiency in amide synthesis.
  • Successful synthesis of an active pharmaceutical ingredient intermediate was achieved.
  • Gram-scale comparison showed improved green metrics over conventional strategies.

Conclusions:

  • Reactive Deep Eutectic Solvents offer a sustainable and efficient alternative for amide synthesis.
  • This approach represents a significant advancement in greening pharmaceutical manufacturing processes.