The base-catalyzed Michael addition of 2-methyl-acryl-amide to benzotriazole afforded 3-(1H-benzotriazol-1-yl)-2-methyl-propanamide, C10H12N4O (1), in 32% yield in addition to small amounts of isomeric 3-(2H-benzotriazol-2-yl)-2-methyl-propanamide, C10H12N4O (2). In a similar manner, 3-(1H-benzotriazol-1-yl)-N,N-di-methyl-propanamide, C11H14N4O (3), was prepared from benzotriazole and N,N-di-methyl-acryl-amide. All three products have been structurally characterized by single-crystal X-ray diffraction. The crystal structures of 1 and 2 comprise infinite arrays formed by N-H⋯O and N-H⋯N bridges, as well as π-π inter-actions, while the mol-ecules of 3 are aggregated to simple π-dimers in the crystal.
Keywords: acrylamide; benzotriazole; benzotriazolylpropanamide; crystal structure; hydrogen bond; π–π stacking.