Ethyl 2-(3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetate

Abstract

The title compound, C7H11N3O2S, exists in the 5-thioxo tautomeric form. The 1,2,4-triazoline ring is essentially planar, with a maximum deviation of 0.010 (2) Å for the substituted N atom. The ethyl acetate substituent is almost planar, with a maximum deviation of 0.061 (4) Å for the methyl­ene C atom of the eth­oxy group. The angle between the mean plane of this substituent and the mean plane of the 1,2,4-triazoline ring is 89.74 (8)°. In the crystal, mol­ecules are linked by a combination of N—H⋯S, C—H⋯N and C—H⋯O hydrogen bonds into chains parallel to [100].

4-Amino-3-(3-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-thione

“…In the title compound ( Fig. 1), the bond lengths and angles have normal values (Allen et al, 1987) and are comparable with closely related structures (Chen et al, 2007;Karczmarzyk et al, 2012;Gao et al, 2011). The angles around atom C3 in the triazole ring deviate from the normal angles based on Csp 2 hybridization, giving bond angles of 102.72 (14)° and 130.12 (13)° for N2-C3-N4 and N2-C3-S1, respectively.…”

“…For the biological activity of 1,2,4-triazole derivatives, see: Cansiz et al (2001); Jones et al (1965); Kane et al (1988); Mullican et al (1993). For related structures, see: Chen et al (2007); Gao et al (2011); Karczmarzyk et al (2012). For standard bond-length data, see: Allen et al (1987).…”

3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

“…For the synthesis, see: Dobosz & Pachuta-Stec (1996). For related structures, see: Karczmarzyk et al (2012); Kruszynski et al (2007); Siwek et al (2008). For graph-set motifs, see Bernstein et al (1995).…”

4-Amino-3-(4-hydroxybenzyl)-1H-1,2,4-triazole-5(4H)-thione

“…For biological properties of 1,2,4-triazole derivatives, see: Holla et al (2001Holla et al ( , 2006; Mullican et al (1993); Jones et al (1965); Shams El-Dine et al (1974); Misato et al (1977); Kane et al (1988). For related structures, see: Puviarasan et al (1999); Chen et al (2007); Karczmarzyk et al (2012); Gao et al (2011).…”

“…The crystal structures of some related triazoles have been reported: 5-(2-Chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4triazole-3-thione (Puviarasan et al, 1999); 4-Amino-5-(2-ethoxyphenyl)-2,4-dihydro-2H-1,2,4-triazole-3-thione-triphenylphosphine oxide (Chen et al, 2007); Ethyl2-(3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetate (Karczmarzyk et al, 2012); 3-(4-Amino-3-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-chlorophenyl)-1-phenylpropan-1-one (Gao et al, 2011). The present work describes the synthesis and crystal structure of the title compound.…”