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1H, triazole-H), 7.60 (d,1H, J ¼ 2.4 Hz, PhH), 7.60 (dd,1H, J1 ¼ 2.4 Hz,
J2 ¼ 8.4 Hz, PhH), 7.54 (dd,1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, PhH), 7.42 (dd,
1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, PhH), 7.37 (d, 1H, J ¼ 8.4 Hz, PhH), 7.05
(dt, 1H, PhH), 4.04 (s, 2H, SeCH2). IR (KBr): 3338 (NH), 1684 (C]O),
1591, 1527, 1496, 1436 (N]N), 1060, 744 (CeS). ESI-MS: m/z 457.0
(M þ 1), 459.0 (M þ 3). C16H11BrCl2N4OS (455.92).
7.91 (d, 1H, J ¼ 8.4 Hz, Ph0H), 7.64 (dd, 1H, J1 ¼ 1.2 Hz, J2 ¼ 8.4 Hz,
PhH), 7.45 (d, 1H, J2 ¼ 8.4 Hz, PhH), 3.85 (s, 2H, SeCH2), 2.58 (s, 3H,
CH3). MS (ESI): m/z 199.1 (M þ 1), 202.1 (M þ 3), 204.1 (Mvþ 5).
C18H13BrCl2N4O2S (497.93).
4.2.12. N-(2-bromo-4-methylphenyl)-2-(2-(2,4-dichlorophenyl)-
2H-1,2,4-triazol-3-ylthio)acetamide (7j)
4.2.6. N-(2,4-dichlorophenyl)-2-(2-(2,4-dichlorophenyl)-2H-1,2,4-
triazol-3-ylthio)acetamide (7d)
White solid, yield: 48.6%. mp: 125e126 ꢀC. 1H-NMR (CDCl3,
ppm)
d
: 9.55 (s, 1H, NH), 8.17 (d, 1H, J ¼ 8.4 Hz, Ph0H), 8.04 (s, 1H,
White needle crystals, yield: 44.7%. mp: 115e118 ꢀC. 1H NMR
triazoleeH), 7.88 (d, 1H, J1 ¼ 1.8 Hz, PhH), 7.59 (dd, 1H, J1 ¼ 1.8 Hz,
J2 ¼ 8.4 Hz, PhH), 7.43 (s, 1H, Ph0H), 7.38 (d, 1H, J ¼ 8.4 Hz, PhH),
7.20 (s, 1H, J ¼ 8.4 Hz, Ph0H), 3.57 (s, 2H, SeCH2), 2.39 (s, 3H, CH3).
MS (ESI): m/z 471.2 (M þ 1), 473.2 (M þ 3). C17H13BrCl2N4OS
(469.94).
(CDCl3, ppm)
d
: 9.90 (s, 1H, NH), 8.26 (d, 1H, J ¼ 9.6 Hz, PhH), 8.07
(s, 1H, triazole-H), 7.43e7.37 (m, 4H, PhH), 7.25 (dd, 1H, J1 ¼ 2.4 Hz,
J2 ¼ 8.4 Hz, PhH), 4.04 (s, 2H, SeCH2). IR (KBr): 3345 (NH), 1692
(C]O), 1580, 1518, 1496, 1413 (N]N), 1385, 1364, 1061, 821, 776
(CeS). ESI-MS: m/z 447.1 (M þ 1), 449.1 (M þ 3). C16H10Cl4N4OS
(445.93).
4.2.13. N-(2-bromo-4-chlorophenyl)-2-(2-(2,4-dichlorophenyl)-
2H-1,2,4-triazol-3-ylthio)acetamide (7k)
4.2.7. N-(2-chloropyridin-3-yl)-2-(2-(2,4-dichlorophenyl)-2H-
1,2,4-triazol-3-ylthio)acetamide (7e)
White solid, yield: 49.8%. mp: 163e165 ꢀC. 1H-NMR (CDCl3,
ppm)
d
: 9.67 (s, 1H, NH), 8.24 (d, 1H, J ¼ 8.4 Hz, Ph0H), 8.08 (s, 1H,
White needle crystals, yield: 65.4%. mp: 143e145 ꢀC. 1H NMR
triazole-H), 7.61 (d, 1H, J ¼ 1.8 Hz, PhH), 7.54 (d, 1H, J ¼ 2.4 Hz,
Ph0H), 7.42 (dd, 1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, Ph0H), 7.38 (d, 1H,
J ¼ 8.4 Hz, PhH), 7.28 (dd, 1H, J1 ¼ 1.8 Hz, J2 ¼ 8.4 Hz, PhH), 4.02 (s,
2H, SeCH2). MS (ESI): m/z 491.1 (M þ 1), 493.1 (M þ 3), 495.0
(M þ 5). C16H10BrCl3N4OS (489.88).
(DMSO, ppm)
d: 10.15 (s, 1H, NH), 8.68 (d, 1H, J ¼ 7.8 Hz, pyridine-
H), 8.28 (d, 1H, J1 ¼1.8 Hz, PhH), 8.20 (dd, 1H, J ¼ 1.2 Hz, J ¼ 4.8 Hz,
pyridine-H), 8.01 (s, 1H, triazole-H), 7.61 (dd, 1H, J1 ¼ 1.8 Hz,
J2 ¼ 8.4 Hz, PhH), 7.40 (d, 1H, J2 ¼ 8.4 Hz, PhH), 7.33e7.29 (m, 1H,
pyridine-H), 4.28 (s, 2H, SeCH2). IR (KBr): 3287 (NH), 1652 (C]O),
1582, 1544, 1520, 1493, 1453 (N]N), 1395, 1072, 809, 799, 785
(CeS). ESI-MS: m/z 414.1 (M þ 1), 416.1 (M þ 3), 418.3 (M þ 3), 436.3
(M þ Naþ), 438.2 (M þ 2 þ Naþ). C15H10Cl3N5OS (412.97).
4.2.14. Methyl 3-bromo-4-(2-(2-(2,4-dichlorophenyl)-2H-1,2,4-
triazol-3-ylthio)acetamido) benzoate (7l)
White needle crystals, yield: 59.3%. mp: 164e166 ꢀC. 1H NMR
(CDCl3, ppm)
d
: 9.84 (s, 1H, NH), 8.24 (d, 1H, J ¼ 8.4 Hz, Ph0H), 8.23
4.2.8. 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-(4-
methyl-2-nitrophenyl)acetamide (7f)
(d, 1H, J ¼ 1.8 Hz, Ph0H), 8.09 (s, 1H, triazole-H), 7.97 (dd, 1H,
J1 ¼ 1.8 Hz, J2 ¼ 8.4 Hz, Ph0H), 7.61 (d, 1H, J ¼ 2.4 Hz, PhH), 7.41 (dd,
1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, PhH), 7.38 (d,1H, J ¼ 8.4 Hz, PhH), 4.05 (s,
2H, SeCH2), 3.91 (s, 3H, OCH3). MS (ESI): m/z 515.3 (M þ 1), 517.4
(M þ 3), 537.0 (M þ Naþ). C18H13BrCl2N4O3S (513.93).
Light yellow powder, yield: 37.4%. mp: 185e186 ꢀC. 1H-NMR
(CDCl3, ppm)
d
: 11.07 (s, 1H, NH), 8.55 (d, 1H, J ¼ 8.4 Hz, PhH), 8.01
(s, 1H, triazole-H), 7.97 (s, 1H, PhH), 7.61 (d, 1H, J ¼ 1.8 Hz, PhH),
7.46e7.42 (m, 3H, PhH), 4.11 (s, 2H, SeCH2), 2.40 (s, 3H, CH3). MS
(ESI): m/z 438.2 (M þ 1), 540.1 (M þ 3). C17H13Cl2N5O3S (437.01).
4.2.15. Ethyl 3-bromo-4-(2-(2-(2,4-dichlorophenyl)-2H-1,2,4-
triazol-3-ylthio)acetamido) benzoate (7m)
4.2.9. 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-(2-
nitrophenyl)acetamide (7g)
White needle crystals, yield: 67.1%. mp: 103e105 ꢀC. 1H-NMR
(CDCl3, ppm)
d
: 9.82 (s, 1H, NH), 8.45 (d, 1H, J ¼ 8.4 Hz, Ph0H), 8.23
Yellow needle crystals, yield: 53.8%. mp: 153e154 ꢀC. 1H-NMR
(d, 1H, J ¼ 1.8 Hz, Ph0H), 8.09 (s, 1H, triazole-H), 7.99 (dd, 1H,
J1 ¼ 1.8 Hz, J2 ¼ 8.4 Hz, Ph0H), 7.61 (d, 1H, J ¼ 2.4 Hz, PhH), 7.42 (dd,
1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, PhH), 7.38 (d,1H, J ¼ 8.4 Hz, PhH), 4.36 (s,
2H, OCH2), 4.05 (s, 2H, SeCH2), 1.39 (s, 3H, CH3). IR (KBr): 3228
(NH), 1720 (C]O), 1684, 1600, 1584, 1529, 1494, 1458 (N]N), 1365,
1285, 1271, 1131, 1106, 763 (CeS). MS (ESI): m/z 529.2 (Mþ1), 531.1
(M þ 3), 533.2 (M þ 5), 551.2 (M þ Naþ), 551.2 (Mþ2 þ Naþ).
C19H15BrCl2N4O3S (527.94).
(CDCl3, ppm)
d
: 11.19 (s, 1H, NH), 8.68 (d, 1H, J ¼ 8.4 Hz, PhH), 8.18
(dd, 1H, J ¼ 1.8 Hz, J ¼ 8.4 Hz, PhH), 8.06 (s, 1H, triazole-H), 7.65 (t,
1H, PhH), 7.61 (d, 1H, J1 ¼1.8 Hz, PhH), 7.46e7.42 (m, 2H, PhH), 7.22
(m, 1H, PhH), 4.13 (s, 2H, SeCH2). IR (KBr): 3295 (NH), 1685 (C]O),
1606, 1585, 1497 (NO2), 1436 (N]N), 1362 (NO2), 1337, 1279, 742
(CeS). MS (ESI): m/z 424.1 (M þ 1), 426.3 (M þ 3). C16H11Cl2N5O3S
(423).
4.2.10. 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-o-
tolylacetamide (7h)
4.2.16. Methyl 4-(2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-
ylthio)acetamido)benzoate (7n)
White lamella crystals, yield: 50.7%. mp: 121e122 ꢀC. 1H-NMR
White needle crystals, yield: 68.2%. mp: 153e154 ꢀC. 1H-NMR
(CDCl3, ppm)
d
: 9.42 (brs, 1H, NH), 8.06 (s, 1H, triazole-H), 7.91 (d,
(CDCl3, ppm) d: 10.43 (s,1H, NH), 8.16 (s,1H, triazole-H), 8.01 (d, 2H,
1H, J1 ¼ 7.8 Hz, PhH), 7.61 (d, 1H, J ¼ 2.4 Hz, Ph0H), 7.43 (dd, 1H,
J1 ¼ 7.8 Hz, J2 ¼ 2.4 Hz, PhH), 7.37 (d, 1H, J2 ¼ 2.4 Hz, PhH), 7.22 (t,
1H, Ph0H), 7.18 (d, 1H, J ¼ 7.2 Hz, Ph0H), 7.08 (t, 1H, Ph0H), 3.96 (s,
2H, SeCH2), 2.27 (s, 3H, CH3). IR (KBr): 3258 (NH), 1687 (C]O),
1591, 1549, 1494, 1458 (N]N), 1365, 1314, 999, 828, 771 (CeS).
MS (ESI): m/z 393.1(M þ 1), 395.1 (M þ 3). C17H14Cl2N4OS
(392.03).
J ¼ 8.4 Hz, Ph0H), 7.64 (d, 2H, J ¼ 8.4 Hz, Ph0H), 7.61 (d,1H, J ¼ 2.4 Hz,
PhH), 7.43 (dd, 1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, PhH), 7.37 (d, 1H,
J ¼ 8.4 Hz, PhH), 3.90 (s, 2H, SeCH2), 3.88 (s, 3H, OCH3). MS (ESI): m/
z 437.3 (M þ 1), 439.3 (M þ 3), 441.4 (M þ 5), 559.3 (M þ Naþ), 461.3
(M þ 2 þ Naþ). C18H14Cl2N4O3S (436.02).
4.2.17. Ethyl 4-(2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-
ylthio)acetamido)benzoate (7o)
4.2.11. N-(4-acetyl-2-bromophenyl)-2-(2-(2,4-dichlorophenyl)-2H-
1,2,4-triazol-3-ylthio)acetamide (7i)
White needle crystals, yield: 71.4%. mp: 147e149 ꢀC. 1H-NMR
(CDCl3, ppm) d: 10.43 (s,1H, NH), 8.16 (s,1H, triazole-H), 8.01 (d, 2H,
White needle crystals, yield: 55.4%. mp: 131e133 ꢀC. 1H-NMR
J ¼ 8.4 Hz, Ph0H), 7.63 (d, 2H, J ¼ 8.4 Hz, Ph0H), 7.61 (d, 1H, J ¼ 2.4 Hz,
PhH), 7.42 (dd, 1H, J1 ¼ 2.4 Hz, J2 ¼ 8.4 Hz, PhH), 7.37 (d, 1H,
J ¼ 8.4 Hz, PhH), 4.35 (s, 2H, OCH2), 4.04 (s, 2H, S-CH2), 1.41 (s, 3H,
(CDCl3, ppm)
d
: 9.27 (s, 1H, NH), 8.36 (d, 1H, J ¼ 8.4 Hz, Ph0H), 8.24
(s, 1H, Ph0H), 8.09 (s, 1H, triazoleeH), 7.98 (d, 1H, J1 ¼ 1.2 Hz, PhH),