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Related Concept Videos

Structure of Amines01:19

Structure of Amines

2.6K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.6K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.7K
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...
3.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.1K
Preparation of Amides01:29

Preparation of Amides

3.2K
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...
3.2K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.5K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.5K
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

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Novel N(SCF3)(CF3)-amines: synthesis, scalability and stability.

Yi Yang1, Nathalie Saffon-Merceron2, Julien C Vantourout1

  • 1Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA 43 Bd du 11 Novembre 1918 69622 Villeurbanne France anis.tlili@univ-lyon1.fr.

Chemical Science
|April 10, 2023
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Summary

Researchers developed a new method to synthesize novel trifluoromethylthio amines. This scalable approach utilizes isothiocyanates and trifluoromethylthiolation reagents, with the stability of the resulting compounds also investigated.

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Synthetic Methodology

Background:

  • Trifluoromethylthio (SCF3) groups are important pharmacophores.
  • Developing efficient synthetic routes to incorporate SCF3 groups remains a challenge.

Purpose of the Study:

  • To develop a straightforward and scalable synthesis for novel N-((trifluoromethyl)thio), N-(trifluoromethyl) amines.
  • To investigate the stability of the newly synthesized compounds.

Main Methods:

  • Reaction of isothiocyanates with a fluoride source.
  • Electrophilic trifluoromethylthiolation using a suitable reagent.
  • Scalability assessment of the synthetic procedure.
  • Stability studies of the target amines.

Main Results:

  • Successful synthesis of unprecedented N-((trifluoromethyl)thio), N-(trifluoromethyl) amines.
  • Demonstration of the scalability of the developed methodology.
  • Characterization and study of the stability of the new amine motif.

Conclusions:

  • A facile and scalable strategy for synthesizing novel trifluoromethylthio amines has been established.
  • The synthesized compounds exhibit notable stability, broadening their potential applications.