Cyanuric acid chloride amides

Cyanuric chloride has been used for the preparation of acyl chlorides, amides, and peptides. Conversion of cyanuric chloride into 2-chloro-4,6-dimethoxy-l,3,5-triazine (CDMT, 6) leads to a reagent that upon reaction with carboxylic acids produces the highly reactive 2-acyloxy-4,6-dimethoxy-l,3,5-triazines.P l The resulting active ester is a powerful acylating agent for alcohols and amines. The activation is performed in presence of a base, preferentially NMM, which leads to intermediate formation of 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM, 7)P l (Scheme 5). This addition product is readily prepared from the commercially available CDMT (6) and NMM in THF and can be stored as solid compound in the cold.P P l It offers the advantage that it can be used in a one-... 

Cyanuric acid amide (melamine, 0.50/lb) can be synthesized by reaction between cyanuric chloride and ammonia [51]. Another method is the trimer-ization of dicyandiamide. However, these reactions have been replaced with... 

Figure 14-1 Functionalization and activation of electrode materials, a) silanization of supports bearing hydroxylic groups b) reaction with cyanuric chloride c) activation with cyanogen bromide d) binding via amide bonds after activation with 1,1-carbonyldiimidazole e) activation with good leaving groups such as tresyl chloride f) formation of Schiff bases between aldehyde groups on the support and amino groups at the biomolecule g) activation of carboxylic groups with carbodiimides or h) via the acid chlorides.

Carboxylic acid fluorides are more stable to water and other nucleophiles. They are readily prepared by the use of cyanuric fluoride and converted to amides by siiylated amines. In contrast to the chlorides, protected amino acid fluorides exert virtually no racemization in peptide coupling. ... 

Cyanuric chloride on monosubstitution with nucleophiles such as methanol or 4-amino-azobenzene followed by displacement of a second chlorine with alanine amide gave compounds which are used for precolumn derivatization of amino acids. The diastereoisomers formed are resolved by reverse-phase HPLC <92MI 6l2-0i>. Enantiomeric amino acids are separated by HPLC on bis[carbamoyl(alkyl)methylamino]-6-chloro-l,3,5-triazine derived stationary phases <93JC277>. 

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