Related Experiment Video
Updated: May 13, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N,N-Diethyl-anilinium 5-(5-chloro-2,4-dinitro-phen-yl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate
1PG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India.
Abstract:
In the anion of the title salt, C10H16N(+)·C10H4ClN4O7(-) [trivial name = N,N-diethyl-anilinium 5-(3-chloro-4,6,-dinitro-phen-yl)barbiturate], the dihedral angle between the benzene and pyrimidine rings is 45.49 (6)°. The mean plane of the nitro group, which is ortho-substituted with respect to the pyrimidine ring, is twisted by 41.57 (13)° from the benzene ring, while the mean plane of the nitro group, which is para-substituted, is twisted by 14.41 (12)° from this ring. In the crystal, N-H⋯O hydrogen bonds link cations and anions into chains along [1-10]. Within the chains, inversion-related anionic barbiturate anions form R2(2)(8) ring motifs.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
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
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Nomenclature of Aryl and Heterocyclic Amines
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

