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Synthesis and Rearrangement of 2-(N-Methyl-N-nitroamino)-4-phenylthiazole

Spaleniak G., Daszkiewicz Z., Kyzio J.

Polish Journal of Chemistry

2007

Vol. 81, nr 2

171-178

2-(N-Methyl-N-nitroamino)-4-phenylthiazole (5) was prepared and rearranged in aqueous dioxane under influence of sulphuric acid of various concentrations. 2-(N-Methylamino)- 5-nitro-4-phenylthiazole (6) was the only product up to 50% acid concentration. At higher acidities, significant amounts of nitro derivatives 3b and3c, substituted in benzene ring, were also formed. The result indicates that migration of the N-nitro group occurs on the intramolecular path, however, in concentrated sulphuric acid, formation of nitronium ion and ring nitration also takes place.