Journal of the Iranian Chemical Society
3H, Ar–H), 3.95 (s, 2H, –CH2–), 2.53 (s, 3H, CH3); 13C
NMR (100 MHz, CDCl3, δ ppm): 166.8, 154.2, 148.4, 137.7,
136.9, 133.1, 132.6, 132.5, 132.3, 131.7, 130.5, 130.4,
129.8, 127.3, 121.4, 119.1, 36.1, 9.5; ESI–MS (m/z): 638.00
[M + NH4]+; Anal. calcd. for C25H16N7Cl4FOS: C, 48.17;
H, 2.59; N, 15.73%. Found: C, 48.15; H, 2.55; N, 15.70%.
ppm): 166.6, 154.1, 148.3, 138.4, 137.4, 136.8, 136.3, 133.1,
132.8, 131.7, 130.5, 130.5, 134.4, 129.7, 122.0, 119.3,
118.9, 36.2, 23.0, 9.5; ESI–MS (m/z): 660.96 [M + H]+;
Anal. calcd. for C26H19N7BrCl3OS: C, 47.04; H, 2.98; N,
14.77%. Found: C, 47.03; H, 2.95; N, 14.72%.
N‑(2‑Fluorophenyl)‑2‑((5‑(5‑methyl‑1‑(2,4,5‑trichloropheny
l)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑triazol‑3‑yl)thio)
acetamide (8i)
2‑((5‑(5‑Methyl‑1‑(2,4,5‑trichlorophenyl)‑1H‑1,2,3‑tria‑
zol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑triazol‑3‑yl)thio)‑N‑(4‑tolyl)
acetamide (8f)
Yield: 65%; Mp. 176–178 °C; Of-white solid; FT-IR (ATR,
υmax, cm−1): 3121 (NH), 2940 (C–H), 1682 (C=O), 1607
(C=N), 1583 (C=C), 766, 820 (C–Cl), 1021 (C–F); 1H NMR
(400 MHz, CDCl3, δ ppm): 10.17 (s, 1H, NH), 8.27–8.30 (m,
1H, Ar–H), 7.72 (s, 1H, Ar–H), 7.51–7.55 (m, 4H, Ar–H),
7.37–7.39 (m, 2H, Ar–H), 7.03–7.13 (m, 3H, Ar–H), 4.07
(s, 2H, –CH2–), 2.16 (s, 3H, CH3); 13C NMR (100 MHz,
CDCl3, δ ppm): 166.8, 153.6, 152.9 (J=200.0 Hz), 148.3,
136.9, 136.2, 133.1 (J = 27.6 Hz), 132.4 (J = 3.3 Hz),
131.7, 130.5, 130.4, 130.3, 129.7, 127.3, 126.6, 126.5,
124.6, 124.5, 124.36, 124.39, 122.0, 114.9 (J = 15.6 Hz),
36.0, 9.5; ESI–MS (m/z): 588.02 [M+H]+; Anal. calcd. for
C25H17N7Cl3FOS: C, 50.99; H, 2.91; N, 16.65%. Found: C,
50.95; H, 2.92; N, 16.63%.
Yield: 88%; Mp. 120–122 °C; Light cream solid; FT-IR
(ATR, υmax, cm−1): 3086 (NH), 2989 (C–H), 1687 (C=O),
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1612 (C=N), 1583 (C=C), 767, 817 (C–Cl); H NMR
(400 MHz, CDCl3, δ ppm): 10.02 (s, 1H, NH), 7.72 (s, 1H,
Ar–H), 7.49–7.54 (m, 6H, Ar–H), 7.36–7.38 (m, 2H, Ar–H),
7.11 (d, 2H, J=8.3 Hz, Ar–H), 3.97 (s, 2H, –CH2–), 2.52 (s,
3H, CH3), 2.30 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3,
δ ppm): 166.4, 154.1, 148.3, 136.8, 136.3, 135.6, 133.8,
133.2, 132.9, 132.5, 132.3, 131.7, 130.5, 130.4, 129.7,
129.3, 127.3, 119.9, 36.1, 20.8, 9.5; ESI–MS (m/z): 584.03
[M + H]+; Anal. calcd. for C26H20N7Cl3OS: C, 53.39; H,
3.45; N, 16.76%. Found: C, 53.30, H, 3.44; N, 16.70%.
N‑(4‑Methoxyphenyl)‑2‑((5‑(5‑methyl‑1‑(2,4,5‑trichlo‑
rophenyl)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑tria‑
zol‑3‑yl)thio)acetamide (8g)
N‑(3‑Chloro‑2‑methylphenyl)‑2‑((5‑(5‑methyl‑1‑(2,4,5‑trich‑
lorophenyl)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑tria‑
zol‑3‑yl)thio)acetamide (8j)
Yield: 75%; Mp. 188–190 °C; Light grey solid; FT-IR (ATR,
υmax, cm−1): 3041 (N–H), 2940 (C–H), 1676 (C=O), 1606
Yield: 65%; Mp. 180–182 °C; Light brown solid; FT-IR
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(C=N), 1552 (C=C), 1082 (C–O), 767, 829 (C–Cl); H
(ATR, υmax, cm−1): 3112 (NH), 2985 (C–H), 1684 (C=O),
1
NMR (400 MHz, CDCl3, δ ppm): 9.98 (s, 1H, NH), 7.72 (s,
1H, Ar–H), 7.50–7.54 (m, 6H, Ar–H), 7.36–7.38 (m, 2H,
Ar–H), 6.83–6.86 (m, 2H, Ar–H), 3.97 (s, 2H, –CH2–), 3.77
(s, 3H, –OCH3–), 2.51 (s, 3H, CH3); 13C NMR (100 MHz,
CDCl3, δ ppm): 166.2, 156.3, 154.1, 148.2, 136.8, 136.3,
133.2, 132.9, 132.5, 132.3, 131.7, 131.4, 130.5, 130.4,
129.7, 127.3, 121.5, 114.0, 55.4, 30.9, 9.5; ESI–MS (m/z):
600.05 [M + H]+; Anal. calcd. for C26H20N7Cl3O2S: C,
51.97; H, 3.35; N, 16.32%. Found: C, 51.95; H, 3.30; N,
16.30%.
1613 (C=N), 1580 (C=C), 764, 815 (C–Cl); H NMR
(400 MHz, CDCl3, δ ppm): 10.23 (s, 1H, NH), 7.89 (s, 1H,
Ar–H), 7.46–7.55 (m, 6H, Ar–H), 6.64–7.29 (m, 3H, Ar–H),
3.68 (s, 2H, –CH2–), 2.56 (s, 3H, CH3), 2.24 (s, 3H, CH3);
13C NMR (100 MHz, CDCl3, δ ppm): 167.2, 144.7, 144.0,
141.9, 141.1, 137.5, 137.4, 137.1, 134.4, 131.7, 129.9, 129.8,
129.3, 129.2, 129.0, 124.8, 124.7, 122.1, 117.7, 117.1, 32.1,
14.6, 9.6; ESI–MS (m/z): 618.01 [M+H]+; Anal. calcd. for
C26H19N7Cl4OS: C, 50.42; H, 3.09; N, 15.83%. Found: C,
50.41; H, 3.08; N, 15.85%.
N‑(4‑Bromo‑3‑methylphenyl)‑2‑((5‑(5‑methyl‑1‑(2,4,5‑tric
hlorophenyl)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑tria‑
zol‑3‑yl)thio)acetamide (8h)
N‑(3,4‑Dimethylphenyl)‑2‑((5‑(5‑methyl‑1‑(2,4,5‑trichlo‑
rophenyl)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑tria‑
zol‑3‑yl)thio)acetamide (8k)
Yield: 72%; Mp. 194–195 °C; Creamish solid; FT-IR (ATR,
υmax, cm−1): 3251 (NH), 2939 (C–H), 1683 (C=O), 1608
(C=N), 1585 (C=C), 765, 819 (C–Cl), 650 (C–Br); 1H NMR
(400 MHz, CDCl3, δ ppm): 10.23 (s. 1H, NH), 7.73 (s, 1H,
Ar–H), 7.50–7.55 (m, 5H, Ar–H), 7.43 (d, 1H, J=8.0 Hz,
Ar–H), 7.32–7.38 (m, 3H, Ar–H), 3.96 (s, 2H, CH2), 2.52 (s,
3H, CH3), 2.37 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3, δ
Yield: 83%; Mp. 132–134 °C; Brown solid; FT-IR (ATR,
υmax, cm−1): 3098 (NH), 2940(C–H), 1681 (C=O), 1609
(C=N), 1583 (C=C), 766, 817 (C–Cl), 1H NMR (400 MHz,
CDCl3, δ ppm): 9.93 (s, 1H, NH), 7.73 (s, 1H, Ar–H),
7.52–7.55 (m, 4H, Ar–H), 7.26–7.39 (m, 4H, Ar–H),
7.05–7.07 (d, 1H, Ar–H), 3.97 (s, 2H, –CH2–), 2.52 (s,
3H, CH3), 2.24 (s, 3H, CH3), 2.17 (s, 3H, CH3); 13C NMR
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