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Journal Article

A solid solution of ethyl and d3-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate


Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Beuchel, A., Goddard, R., Imming, P., & Seidel, R. W. (2020). A solid solution of ethyl and d3-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate. Acta Crystallographica Section E: Structure Reports Online, 76(8), 1255-1259. doi:10.1107/S2056989020008956.

Cite as: https://hdl.handle.net/21.11116/0000-0007-45F3-9
The synthesis of ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-
5-carboxylate via the Hantzsch reaction and partial in situ transesterification
during recrystallization from methanol-d4 to the d3-methyl ester, resulting in the
title solid solution, ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thia-
zole-5-carboxylate–d3-methyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate (0.88/0.12), 0.88C17H16N4O2S∙0.12C16D3H11N4O2S, is
reported. The refined ratio of ethyl to d3-methyl ester in the crystal is 0.880 (6):0.120 (6). The pyridine ring is significantly twisted out of the plane of
the approximately planar picoline thiazole ester moiety. N—H∙ ∙ ∙N hydrogen
bonds between the secondary amino group and the pyridine nitrogen atom of an
adjacent symmetry-related molecule link the molecules into polymeric hydrogen-bonded zigzag tapes extending by glide symmetry in the [001] direction. There is structural evidence for intramolecular N∙ ∙ ∙S chalcogen bonding and intermolecular weak C—H∙ ∙ ∙O hydrogen bonds between adjacent zigzag tapes.