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Related Concept Videos

Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...
Preparation of Amides01:29

Preparation of Amides

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

Preparation of 1° Amines: Azide Synthesis

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...
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

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Related Experiment Video

Updated: May 16, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
12:02

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

Three new amides from Microlepia pilosissima.

Jiang Hu1, Xiao-Dong Shi, Jian-Gang Chen

  • 1College of Biological Resources and Environment Science, Qujing Normal University, Qujing 655011, China. hujiang@ustc.edu

Journal of Asian Natural Products Research
|November 21, 2012
PubMed
Summary

Three novel amides were isolated from the fern Microlepia pilosissima. Spectroscopic analysis confirmed the structures of these new phytochemical compounds.

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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
13:37

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

Published on: June 20, 2014

Related Experiment Videos

Last Updated: May 16, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
12:02

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
13:37

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

Published on: June 20, 2014

Area of Science:

  • Phytochemistry
  • Natural Products Chemistry
  • Organic Chemistry

Background:

  • The fern Microlepia pilosissima is a potential source of bioactive compounds.
  • Ethnobotanical uses suggest the presence of unique chemical constituents.

Purpose of the Study:

  • To isolate and characterize new amide compounds from Microlepia pilosissima.
  • To elucidate the structures of these novel phytochemicals using advanced spectroscopic techniques.

Main Methods:

  • Extraction of dry fronds of Microlepia pilosissima using 70% ethanol.
  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation via 1D NMR, 2D NMR, and High-Resolution Electrospray Ionization Mass Spectrometry (HR-ESI-MS).

Main Results:

  • Three new amides were successfully isolated and identified.
  • Compound 1: (7E)-N-(3'-hydroxyl-4'-methoxy)-phenylethyl-4-hydroxyl-cinnamamide.
  • Compounds 2 and 3: (7E)-N-(3',4',5'-trihydroxyl)-phenylethyl-4-hydroxyl-cinnamamide and (7E)-N-(3',4',5'-trihydroxyl)-phenylethyl-4-methoxy-cinnamamide, respectively.

Conclusions:

  • The phytochemical investigation led to the discovery of three previously undescribed amide compounds.
  • The structural characterization confirms the presence of unique chemical entities in Microlepia pilosissima.
  • This study expands the knowledge of the chemical diversity within the Microlepia genus.