Preparation of Several Active N-Chloro Compounds from Trichloroisocyanuric
Acid

Azam Shiri; Ahmad Khoramabadi-zad

doi:10.1055/s-0029-1216889

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Synthesis 2009(16): 2797-2801
DOI: 10.1055/s-0029-1216889

PAPER

Preparation of Several Active N-Chloro Compounds from Trichloroisocyanuric Acid

Azam Shiri, Ahmad Khoramabadi-zad*
Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 6517838683, Hamadan, Iran
Fax: +98(811)8257407; e-Mail: khoram@basu.ac.ir;

Further Information

Publication History

Received 7 April 2009
Publication Date:
07 July 2009 (online)

Abstract
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Abstract

A very simple method for the preparation of several active N-chloro compounds that have extensive applications in organic synthesis, industry, and medicine has been developed. Tetrachloroglycolurils, chloramine-T, N-chlorosaccharin, N-chlorosuccinimide, N-chlorophthalimide, N,N′-dichlorophenobarbital, and N,N′-dichlorobarbital were synthesized by chlorination with trichloroisocyanuric acid under mild reaction conditions at room temperature. This method is clean, fast, and efficient; the yields are also good to excellent.

Key words

chlorinated compounds - imides - amides - halogenation - trichloroisocyanuric acid

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These compounds have been extensively investigated since their discovery by Schiff in 1877. Glycoluril (IUPAC name: perhydroimidazo[4,5-d]imidazole-2,5-dione) and its derivatives are heterocyclic compounds that have found a number of applications, including polymer cross-linking, explosives, stabilizers of organic compounds against photodegradation, and combinatorial chemistry. Glycoluril has also been used as a building block for various supramolecular objects. Among others, the groups of Rebek,^³² Nolte,^³³ and Isaacs^³4 have extensively studied the synthesis and behavior of a wide variety of glycoluril derivatives.