Alkylation of cyclic mannich bases, derivatives of thiourea and simple amino acids

Aminomethylation of thiourea with aqueous formaldehyde and simple amino acids (glycine, β-alanine, γ-aminobutyric acid) have resulted in the formation of (4-thioxo-1,3,5-triazinan-1-yl)-substituted acetic, propionic, and butyric acids, respectively. By alkylation of these compounds corresponding S -methyl and S -ethyl iodides were obtained, and by the action of tert -butylamine, the corresponding salts. The same salts were obtained by the reaction of amine exchange between 5- tert -butyl-1,3,5-triazinan-2-thione and these amino acids in water. As a result of neutralization of S -methyl iodides with tert -butylamine in 2-propanol or aqueous 2-propanol zwitterionic [4-(methyl-sulfanyl)-3,6-dihydro-1,3,5-triazin-1(2 H )-yl] derivatives of these acids were isolated. From aqueous solutions of S -methyl iodides and tert -butylamine ion associates of the corresponding zwitter-ions and tert -butylammonium iodide have crystallized. The same associates have formed at treating S -methyl iodides with tert -butylamine or diethylamine in the absence of a solvent.