A facile preparation of (2,4,6‐¹⁴C)‐cyanuric acid under solvent‐free conditions

Abstract

Summary(2,4,6-14 C)-Cyanuric acid was prepared from 14 C-urea by the heterocyclization of the latter in the presence of ammonium chloride. This procedure involves solvent-free fusing of the reactants in a vacuum sealed glass tube. The product was purified by ion-exchange column chromatography using Sephadex SE C-25. A radiochemical yield of 60.5% was obtained based on 14 C-urea and the product had a specific activity of 19.06 mCi/mmol.

Weak Intermolecular CH···N Hydrogen Bonding: Determination of 13CH–15N Hydrogen-Bond Mediated J Couplings by Solid-State NMR Spectroscopy and First-Principles Calculations

“…In overview, [ 15 N 3 ]-cyanuric acid ( 4 ) was obtained by cyclotrimerization of [ 15 N 2 ]-urea ( 3 ), and then nucleophilic substitution of the hydroxyl groups by chlorine gave the [ 15 N 3 ]-cyanuric chloride or [ 15 N 3 ]-2,4,6-trichloro-1,3,5-triazine ( 5 ). Treatment of lithium 2-(trimethylsilyl)­acetylide ( 7 ) with a solution of anhydrous zinc chloride in tetrahydrofurane yielded [ 13 C 2 ]-[(trimethylsilyl)­ethynyl]­zinc chloride ( 8 ), , which was reacted with [ 15 N 3 ]-2,4,6-trichloro-1,3,5-triazine ( 5 ) in the presence of tetrakis­(triphenylphosphine)­palladium to afford [ 15 N 3 , 13 C 6 ]-2,4,6-tris­[(trimethylsilyl)­ethynyl]-1,3,5-triazine ( 9 ). , Further hydrolysis of the latter compound with potassium fluoride in CH 3 OH–THF resulted in [ 15 N 3 , 13 C 6 ]-2,4,6-triethynyl-1,3,5-triazine ( 2- 15 N 3 , 13 C 6 ).…”

Liquid-Phase Synthesis of Cyanuric Acid from Urea

“…It is also the raw material for many new products such as trichloroiminocyanuric acid (TCCA), 1,3,5-tri-2–propenyl-1,3,5–triazine-2,4,6-(1 H ,3 H ,5 H )-trione (TAIC), triglycidyl isocyanurate (TGIC) and tricarboxylethyl isocyanurate (TCIC). These new products are well known and widely used in chemical engineering, light manufacturing, electrical appliances, mechanical industry, spinning and agriculture [ 1 , 2 , 3 , 4 ].…”