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Preparation of 1° Amines: Azide Synthesis

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...

Preparation of 1° Amines: Gabriel Synthesis

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 and Reactions of Sulfides

Preparation and Reactions of Sulfides

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.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Acid Halides to Amides: Aminolysis

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...

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Related Experiment Video

Updated: Mar 27, 2026

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Published on: January 3, 2018

Aqueous Compatible Protocol to Both Alkyl and Aryl Thioamide Synthesis.

Jianpeng Wei¹, Yiming Li¹, Xuefeng Jiang^1,2

¹Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University , Shanghai 200062, P. R. China.

Organic Letters

|January 7, 2016

Summary

A new aqueous synthesis method efficiently creates thioamides from aldehydes and sodium sulfide. This practical approach is useful for modifying bioactive molecules.

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Published on: August 1, 2018

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Thioamides are important functional groups in medicinal chemistry and materials science.
Existing thioamide synthesis methods often require harsh conditions or toxic reagents.

Purpose of the Study:

To develop an efficient and practical aqueous synthesis of thioamides.
To explore the use of readily available starting materials and mild reaction conditions.

Main Methods:

A one-pot reaction involving aldehydes, sodium sulfide (Na2S), and N-substituted formamides in water.
Utilizing sodium sulfide as a cost-effective and accessible sulfur source.
Investigating the scope of the reaction with various alkyl and aryl aldehydes.

Main Results:

Successful synthesis of diverse thioamides with high yields.
Demonstration of the method's applicability to both alkyl and aryl aldehydes.
Establishment of late-stage functionalization of bioactive molecules using this protocol.

Conclusions:

The developed aqueous method provides an efficient and practical route to thioamides.
N-substituted formamides are crucial for this transformation.
This protocol offers a greener and more accessible alternative for thioamide synthesis, including for complex molecules.