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], C(13)H(16)N(5)O(2)S, exists in the 3-aryl-5-thio-ureido-1H-1,2,4-triazole tautomeric form. The mol-ecular structure is stabilized by intra-molecular hydrogen bonding (N-H⋯S=C between the endocyclic N-bound H atom and the thio-ureido S atom, and N-H⋯O=C within the ethoxy-carbonyl-thio-urea 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 mol-ecules form two types of centrosymmetric dimers connected by inter-molecular hydrogen bonds; in the first, the N-NH triazole sides of two mol-ecules are connected [R(2) (2)(6) graph-set motif] and the second is an N-H⋯S=C inter-action between the imide H atoms and the thio-carbonyl S atoms [R(2) (2)(8) graph-set motif]. Together, they form a network parallel to the (111) plane.

Fig. 1.

The molecular structure of I with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 2.

Crystal packing in the cell viewed along the axis c.

Fig. 3.

Synthesis of N-carbethoxy-N'-[3-(4-methylphenyl)-1H-1,2,4-triazol-5- yl]thiourea.

Fig. 4.

Annular tautomerism in N-carbethoxy-N'-[3(5)-(4-methylphenyl)-1(4)H-1,2,4-\ triazol-5(3)-yl]thiourea.