Cyan uric chloride

The 1,3,5-triazines are amongst the oldest known organic molecules. Originally they were called the symmetric triazines, usually abbreviated to s- or sym- triazines. The numbering follows the usual convention of beginning at the heteroatom as shown for the parent compound 1,3,5-triazine (1). Rather non-systematic nomenclature is prevalent even in the current literature, because some of the compounds have been known for at least 150 years. The non-systematic names of some of the more important 1,3,5-triazines are listed in Table 1. The terms melamine, cyanuric acid and cyan uric chloride will be used throughout this chapter, and the term triazine will refer to 1,3,5-triazines only. In addition to the above names, 2,4,6-trialkoxy-l,3,5-triazines (2) are called cyanurates. Similarly, 1,3,5-trialkyl-1,3,5-triazines (3) are called isocyanurates. 

Other 7- substituents that have been introduced include the dialkylamino, acctamido, hydroxy, alkoxy and alkylthio groups . Acylation of the 7-amino group by heterocycles such as cyan uric chloride and its derivatives was inevitable, as was incorporation of a 7-triazole substitution pattern by diazotization of the 7-amino group and o-coupling with 2-naphthylamine followed by triazolization (94). 

Alkyl thiols and cyan uric chloride react in the presence of a base to form 2-(alkylsulfanyl)-4,6-dichloro-1.3,5-triazines 14l00,101 or2,4-bis(alkylsulfanyl)-6-chloro-1,3,5-tria7ines. These compounds act as starting materials in the production of pesticides, dyestuffs, and rubber chemicals. 

Triaryloxy-l,3,5-triazines 783 are important chemicals used in various fields such as polymers, dyes, and pharmaceuticals. In view of their potential applications, a rapid synthesis of 783 in excellent yields (85-90%) was reported by heating cyan-uric chloride (782) with the sodium salt of phenolic compounds in water by using focused MW. Moreover, it was considered to be an environmental friendly procedure (Scheme 150) (00SC1719). 

Triamino-l,3,5-triazine (melamine) and 2,4,6-trichloro-l,3,5-triazine (cyan-uric chloride) are important chemical intermediates. 

In addition to acyl chlorides of the usual type, the acid chloride of cyan-uric acid C3N3CI3 reacts with NaMn(CO)s to form an acyl derivative C3N3Cl[Mn(CO)5]2 (104). In this reaction only two of the three available chlorine atoms are replaced by manganese pentacarbonyl residues. 

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