NITROGEN HETEROCYCLIC DERIVATIVES
1573
5-(1H-Benzimidazol-2-yl)-4-((4-hydroxybenzylidene)amino)-4H-[1◦,2,4]triazole-
1
3-thiol (Compound 9f): Light yellow solid; yield: 89.3%; mp: 236–237 C; H NMR
(DMSO-d6) δ/ppm: 14.45 (s, 1H, –SH), 13.25 (s, 1H, –NH), 10.41 (s, 1H, –N = CH–)
9.20 (s, 1H, -ArOH), 7.81 (d, J = 8.4 Hz, 2H, Ph–H), 7.67 (d, J = 8.0 Hz, 2H, Ph–H),
7.57 (d, J = 8.0 Hz, 1H, Ph–H), 7.32 (d, J = 7.6Hz, 1H, Ph–H), 7.23 (t, J = 7.6 Hz, 1H,
Ph–H), 6.94 (t, J = 8.0 Hz, 1H, Ph–H); 13C NMR (DMSO-d6) δ/ppm: 163.9, 162.5, 158.9,
141.8, 139.4, 138.9, 131.9, 124.7, 122.9, 116.5, 112.6; FT-IR (KBr) ν/cm−1: 3428, 3350,
2608, 1604, 1570, 1516, 1482, 828, 745; ESI-MS m/z: 337.1 [M+H]+, 359.1 [M+Na]+;
HR-MS: calcd for C16H13N6OS [M+H]+ 337.0870, found 337.0879.
5-(1H-Benzimidazol-2-yl)-4-((4-methylbenzylidene)amino)-4H-[1,2,4]triazole-
◦
1
3-thiol (Compound 9g): Light yellow solid; yield: 91.3%; mp: 212–214 C; H NMR
(DMSO-d6) δ/ppm: 14.51(s, 1H, –SH), 13.29 (s, 1H, –NH), 9.39 (s, 1H, –N = CH–),
7.87 (d, J = 7.6 Hz, 2H, Ph–H), 7.66 (d, J = 8.0 Hz, 1H, Ph–H), 7.58 (d, J = 8.0 Hz,
1H, Ph–H), 7.40 (d, J = 7.6 Hz, 2H, Ph–H), 7.32 (t, J = 7.4 Hz, 1H, Ph–H), 7.23 (t,
J = 7.4 Hz, 1H, Ph–H), 2.42 (s, 3H, CH3); 13C NMR (DMSO-d6) δ/ppm: 165.9, 163.9,
143.8, 141.8, 139.3, 138.9, 130.2, 129.8, 129.6, 122.5, 112.4, 21.8; FT-IR (KBr) ν/cm−1
:
3362, 2367, 1648, 1600, 1566, 1534, 1479, 814, 752; ESI-MS m/z: 335.2 [M+H]+, 357.2
[M+Na]+; HR-MS: calcd for C17H15N6S [M+H]+ 335.1079, found 335.1077.
5-(1H-Benzimidazol-2-yl)-4-((4-bromobenzylidene)amino)-4H-[1,2,4]triazole-
3-thiol (Compound 9h): Yellow solid; yield: 90.5%; mp: 193–195 ◦C; 1H NMR
(DMSO-d6) δ/ppm: 14.56 (s, 1H, –SH), 13.32 (s, 1H, –NH), 9.52 (s, 1H, –N CH–), 7.93
(d, J = 8.0 Hz, 2H, Ph–H), 7.81 (d, J = 8.4 Hz, 2H, Ph–H), 7.66 (d, J = 8.0 Hz, 1H,
Ph–H), 7.58 (d, J = 7.6 Hz, 1H, Ph–H), 7.33 (t, J = 7.4 Hz, 1H, Ph–H), 7.24 (t, J 7.4 Hz,
1H, Ph–H); 13C NMR (DMSO-d6) δ/ppm: 165.9, 163.8, 141.8, 141.1, 138.8, 132.7, 131.3,
128.9, 125.6, 122.6, 112.4; FT-IR (KBr) ν/cm−1: 3340, 2402, 1644, 1589, 1524, 1478,
818, 747, 527; ESI-MS m/z: 399.0, 401.0 [M+H]+, 421.1, 423.0 [M+Na]+; HR-MS: calcd
for C16H12BrN6S [M+H]+ 399.0028, found 399.0027.
5-(1H-Benzimidazol-2-yl)-4-((3-bromobenzylidene)amino)-4H-[1,2,4]triazole-
3-thiol (Compound 9i): Yellow solid; yield: 88.3%; mp: 170–172 ◦C; 1H NMR
(DMSO-d6) δ/ppm: 14.58 (s, 1H, –SH), 13.31 (s, 1H, –NH), 9.49 (s, 1H, –N CH–), 8.19
(s, 1H, Ph–H), 7.98 (d, J = 7.6 Hz, 1H, Ph–H), 7.88 (m, 1H, Ph–H), 7.68 (d, J = 8.4 Hz,
1H, Ph–H), 7.56 (m, 2H, Ph–H), 7.34 (t, J = 7.6 Hz, 1H, Ph–H), 7.25 (t, J = 7.8 Hz, 1H,
Ph–H); 13C NMR (DMSO-d6) δ/ppm: 166.0, 163.8, 141.9, 141.1, 138.7, 135.8, 134.7,
131.6, 129.7, 128.7, 124.4, 122.7, 111.7; FT-IR (KBr) ν/cm−1: 3320, 2419, 1649, 1592,
1534, 1482, 793, 731, 528; ESI-MS m/z: 399.0,401.0 [M+H]+, 421.1,423.0 [M+Na]+.
5-(1H-Benzimidazol-2-yl)-4-((2-bromobenzylidene)amino)-4H-[1,2◦,4]triazole-
1
3-thiol (Compound 9j): Light yellow solid; yield: 90.8%; mp: 179–181 C; H NMR
(DMSO-d6) δ/ppm: 14.60 (s, 1H, –SH), 13.28 (s, 1H, –NH), 10.13 (s, 1H, –N CH–), 8.24
(t, J = 4.2 Hz, 1H, Ph–H), 7.85 (t, J = 4.0 Hz, 1H, Ph–H), 7.72 (d, J = 8.0 Hz, 1H, Ph–H),
7.59 (d, J = 5.2 Hz, 3H, Ph–H), 7.34 (t, J = 7.6 Hz, 1H, Ph–H), 7.26 (t, J = 7.6 Hz, 1H,
Ph–H); 13C NMR (DMSO-d6) δ/ppm: 165.2, 163.5, 142.2, 139.4, 138.8, 134.9, 134.0,
131.7, 129.3, 128.9, 126.1, 123.0, 112.7; FT-IR (KBr) ν/cm−1: 3383, 3246, 2424, 1645,
1588, 1529, 1479, 748, 528; ESI-MS m/z: 399.0, 401.0 [M+H]+, 421.1, 423.0 [M+Na]+.
5-(1H-Benzimidazol-2-yl)-4-((4-fluorobenzylidene)amino)-4H-[1,2,4]triazole-3-
thiol (Compound 9k): White solid; yield: 94.6%; mp: 203–204 ◦C; 1H NMR (DMSO-d6)
δ/ppm: 14.54 (s, 1H, –SH), 13.31 (s, 1H, –NH), 9.49 (s, 1H, –N CH–), 8.06 (dd, J1 =
6.0 Hz, J2 = 8.4 Hz, 2H, Ph–H), 7.66 (d, J = 8.0 Hz, 1H, Ph–H), 7.58 (d, J = 8.0 Hz,
1H, Ph–H), 7.45 (t, J = 8.8 Hz, 2H, Ph–H), 7.33 (t, J = 7.6 Hz, 1H, Ph–H), 7.22