(Z)-3-p-Tolyl-2-(p-tolyl-imino)-1,3-thia-zolidin-4-one
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Updated: May 22, 2026

10:42
Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Abstract:
In the title compound, C(17)H(16)N(2)OS, the central thia-zolidin-4-one ring forms dihedral angles of 66.49 (9) and 79.45 (6)° with the two methyl-substituted benzene rings. In the crystal, mol-ecules are stacked in columns along the b axis through C-H⋯π inter-actions. The H atoms of one of the methyl groups are disordered over two orientations with equal site occupancies.
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Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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