High nitrogen chemistry: Synthesis and properties of N,N-bis(4,5-dicyano-1-methyl-2-imidazolyl)cyanamide and N,N,N′,N′,N″,N″-hexakis(4,5-dicyano-1-methyl-2-imidazoly)melamine

✍ Scribed by Ramachandran P Subrayan; Paul G Rasmussen

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 355 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01058-8

✦ Synopsis

Cyanation of bis(4,5-dicyano-l-methyl-2-imidazolyl)arnine(1) using cyanogen chloride gave N,N-bis(4,5-dicyano-l-methyl-2-imidazolyl)cyanamide(3) as a light yellow solid. Compound 3 is themmlly labile and upon heating the N-CN bond is cleaved and the reactive amine intermediate readily reacts with the moisture giving 1. Nucleophilic aromatic substitution(SNAr ) reaction of the sodium salt of 1 with cyanuric chloride gave N,N,N',N',N",N"-hexald~4,5-dicyano-l-methyl-2-imidazolyl)melamlne( 5), as a white microctystallme solid. Compound 5 is thermally stable up to 300 °C in nitrogen and air. Compound S showed strong emission bands at 476 nm in acetonilrile and 448 nm in DMF. Therefore, 5 may be used as a fluorescent probe.