1-[(1-Ethoxypropylidene)amino]-2-ethyl-4-(4-hydroxybenzyl)imidazol-5(4H)-one
The racemic title compound, C17H23N3O3, isolated from the reaction of L-(−)-tyrosine hydrazide with triethyl orthopropionate in the presence of a catalytic quantity ofp-toluenesulfonic acid (p-TsOH), crystallizes withZ′ = 1 in a centrosymmetric monoclinic unit cell. The molecule contains two planar fragments,viz.the benzene and imidazole rings, linked by two C—C single bonds. The dihedral angle between the two planes is 59.54 (5)° and the molecule adopts a synclinal conformation. The HOMA (harmonic oscillator model of aromaticity) index, calculated for the benzene ring, demonstrates no substantial interaction between the two π-electron delocalization regions in the molecule. In the crystal structure, there is an O—H...N hydrogen bond that links the molecules along thecaxis.