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Related Concept Videos

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K
Preparation of Nitriles01:12

Preparation of Nitriles

2.2K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.2K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.0K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.8K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.6K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.6K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.1K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
3.1K

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N,N-Disubstituted Anilines Synthesis through Smiles Rearrangement.

Sukhendu Pramanick1, Sudipta Baur1, Kartik Rustagi1

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The Journal of Organic Chemistry
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A new metal-free method synthesizes N-substituted anilines using sulfonyl chlorides and amines. This efficient and scalable process offers broad functional group tolerance for creating complex aniline derivatives.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • N-substituted anilines are crucial building blocks in pharmaceuticals and materials science.
  • Existing synthetic methods often require harsh conditions or transition metal catalysts.

Purpose of the Study:

  • To develop a general, mild, and metal-free synthetic route to N-substituted anilines.
  • To demonstrate the broad applicability and scalability of the developed method.

Main Methods:

  • Reaction of sulfonyl chlorides with amines under mild, metal-free conditions.
  • Utilizing readily available starting materials for efficient synthesis.

Main Results:

  • Successfully synthesized a wide range of N-substituted anilines.
  • Demonstrated excellent functional group tolerance and operational simplicity.
  • Confirmed the scalability of the synthetic approach.

Conclusions:

  • The reported method provides an effective and versatile tool for synthesizing N-substituted anilines.
  • This metal-free approach offers advantages in terms of sustainability and cost-effectiveness for accessing functionalized aniline products.