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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...

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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: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Adamantane-1-thio-amide.

Maryam Zahid, M Khawar Rauf, Michael Bolte

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a key intermediate, C(11)H(17)NS, crucial for synthesizing biologically active adamantylthiazolo-oxadiazoles. The adamantyl group exhibits disorder, and the structure is stabilized by intermolecular N-H⋯S hydrogen bonds.

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Area of Science:

Organic Chemistry
Crystallography
Medicinal Chemistry

Background:

Adamantylthiazolo-oxadiazoles are a class of biologically active compounds.
Efficient synthesis of these compounds requires specific chemical intermediates.
Understanding the structural properties of intermediates is vital for synthesis optimization.

Purpose of the Study:

To determine the crystal structure of the title compound, C(11)H(17)NS.
To elucidate the structural features, including adamantyl residue disorder and intermolecular interactions.
To provide foundational data for the synthesis of biologically active adamantylthiazolo-oxadiazoles.

Main Methods:

Single-crystal X-ray diffraction analysis was performed on the title compound.
The crystal structure was solved and refined to determine atomic positions and bonding.
Analysis of the crystal packing and intermolecular interactions was conducted.

Main Results:

The crystal structure of C(11)H(17)NS was successfully determined.
The adamantyl residue was found to be disordered over two sites with specific site-occupation factors (0.817(3) and 0.183(3)).
Intermolecular N-H⋯S hydrogen bonds were identified as the primary stabilizing interactions in the crystal lattice.

Conclusions:

The determined crystal structure provides critical insights into the molecular arrangement of C(11)H(17)NS.
The observed adamantyl residue disorder and hydrogen bonding patterns are key structural characteristics.
This structural information supports its role as a valuable intermediate in the synthesis of novel pharmaceuticals.