N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea

Abstract

The title compound, [systematic name: ethyl ({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate], C13H16N5O2S, exists in the 3-aryl-5-thio­ureido-1H-1,2,4-triazole tautomeric form. The mol­ecular structure is stabilized by intra­molecular hydrogen bonding (N—H⋯S=C between the endocyclic N-bound H atom and the thio­ureido S atom, and N—H⋯O=C within the ethoxy­carbonyl­thio­urea unit), both arranged in an S(6) graph-set motif. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 6.59 (10)°. In the crystal structure, the mol­ecules form two types of centrosymmetric dimers connected by inter­molecular hydrogen bonds; in the first, the N—NH triazole sides of two mol­ecules are connected [R 2 2(6) graph-set motif] and the second is an N—H⋯S=C inter­action between the imide H atoms and the thio­carbonyl S atoms [R 2 2(8) graph-set motif]. Together, they form a network parallel to the (111) plane.

A monoclinic polymorph ofN-ethoxycarbonyl-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

“…2 and Table 1) are arranged in a S6 graph-set motif (Bernstein et al, 1995) stabilizing the tautomer structure. The general configurations of the carbethoxythiourea group in the title molecule replicate that of previously reported for triclinic polymorph (Dolzhenko et al, 2010a) and a similar structure (Dolzhenko et al, 2010b).…”

“…For the crystal structure of the triclinic polymorph, see: Dolzhenko et al (2010a). For the crystal structure of Ncarbethoxy-N 0 -(3-aryl-1H-1,2,4-triazol-5-yl)thiourea, see: Dolzhenko et al (2010b). For the graph-set analysis of hydrogen bonding, see: Bernstein et al (1995).…”

4-{3-[Hydroxy(phenyl)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl}benzenesulfonamide

“…Previous reports have also dealt with the annular tautomerism encountered in 1,2,4-triazoles in the solid state and in solution (Buzykin et al, 2008;Dolzhenko et al, 2010). For 3(5)-thioxo-1,2,4-triazoles, two tautomeric forms may exist in the solid state: the thione (C=S) and the thiol (SH), where the former has been supported by a recent X-ray diffraction study (Karayel et al, 2007).…”

“…For the pharmacological activity of functionalized 1,2,4-triazoles, see: De La Rosa et al (2006); Mavrova et al (2009); Shiradkar et al (2007). For annular tautomerism in 1,2,4triazoles in the solid state and in solution, see: Buzykin et al (2008); Dolzhenko et al (2010). Two tautomeric fothione (C=S)r.m.s.…”

Discovery of Protease-Activated Receptor 4 (PAR4)-Tethered Ligand Antagonists Using Ultralarge Virtual Screening

“…49 The cyclization to the 3-amino-1H-1,2,4triazoles was performed according to. 50 Fluorine containing carboxylic acids was prepared from the appropriate fluoroanilines according to. 51 General Procedure for the Amide Coupling of the Final Compounds.…”