Journal of the Iranian Chemical Society
(s, 2H, H-2″), thiophene-H [6.86 (d, J= 2.8 Hz, 1H, H-3′),
6.90 (dd, J = 3.0, 2.8 Hz, 1H, H-4″), 7.18 (d, J = 3.0 Hz,
1H, H-5′)], Ar–H [7.23–7.26 (m, 3H, H-3′-5′), 7.80 (s,
1H, NH); 13C-NMR (125 MHz, CDCl3): δ 13.6 (CH3),
16.2 (CH3), 20.1 (CH3), 30.1 (C-6′), 36.3 (C-2″), 42.5
(CH2), thiophene-C [126.6 (C-4′), 130.0 (C-3′), 134.9
(C-5′), 136.1 (C-2′)], Ar–C [125.0 (C-5‴), 125.2 (C-3‴),
126.2 (C-4‴), 126.8 (C-2‴), 129.0 (C-6‴, 137.3 (C-1‴)],
150.5 (C-5), 154.6 (C-3), 167.3 (C-1″); HR-EI-MS (m/z):
386.1224 [M]+ calculated for C19H22S2N4O; 386.1235.
125.4 (C-5‴), 125.8 (C-6‴), 130.4 (C-2‴), 135.7 (C-3‴),
137.9 (C-1‴)], 151.0 (C-5), 155.0 (C-3), 166.9 (C-1″); HR-
EI-MS (m/z): 386.1226 [M]+ calculated for C19H22S2N4O;
386.1235.
N‑(2,4‑dimethylphenyl)‑2‑(4‑ethyl‑5‑(thiophen‑2‑ylmethyl)‑
4H‑1,2,4‑triazol‑3‑ylthio)acetamide (9b)
Amorphous powder; yield: 69%; M.P.: 129–130 °C; IR
(KBr) vmax: 3030, 2915, 1696, 1596, 1535 cm−1; 1H-NMR
(500 MHz, CDCl3): δ 1.12 (t, J=6.5 Hz, 3H, CH3–CH2–N),
2.11 (s, CH3, 3H), 2.24 (s, CH3, 3H), 3.81 (q, J=6.5 Hz, 2H,
CH3–CH2–N), 4.00 (s, 2H, H-6′), 4.13 (s, 2H, H-2″), thio-
phene-H [6.57 (d, J=2.8 Hz, 1H, H-3′), 6.98 (dd, J=3.0,
2.8 Hz, 1H, H-4′), 7.18 (d, J = 3.0 Hz, 1H, H-5′)], Ar–H,
[7.23 (br s, 1H, H-3‴), 7.33 (d, J=8.0 Hz, 1H, H-5‴), 7.38
(d, J = 8.0 Hz, 1H, H-6‴)], 7.98 (s, 1H, NH); 13C-NMR
(125 MHz, CDCl3): δ 13.6 (CH3), 16.2 (CH3), 20.1 (CH3),
31.1 (C-6′), 36.5 (C-2″), 44.4 (CH2), 126.4 (C-4′), 130.1
(C-3′), 132.5 (C-5′), 138.2 (C-2′), Ar–C [126.1 (C-5‴),
127.2 (C-6‴), 127.2 (C-3‴), 128.4 (C-2‴), 129.6 (C-4‴),
136.7 (C-1‴)], 151.6 (C-5), 155.0 (C-3), 166.5 (C-1″); HR-
EI-MS (m/z): 386.1224 [M]+ calculated for C19H22S2N4O;
386.1235.
N‑(3,4‑dimethylphenyl)‑2‑(4‑ethyl‑5‑(thiophen‑2‑ylmethyl)‑
4H‑1,2,4‑triazol‑3‑ylthio)acetamide (9e)
Amorphous powder; yield: 69%; M.P.: 127–129 °C; IR
1
(KBr) vmax: 3026, 2928, 1693, 1591, 1535 cm−1; H-
NMR (500 MHz, CDCl3): δ 1.04 (t, J = 6.5 Hz, 3H,
CH3–CH2–N), 1.94 (s, 3H, CH3), 2.03 (s, 3H, CH3), 3.80
(q, J = 6.5 Hz, 2H, CH3–CH2–N), 4.02 (s, 2H, H-6′),
4.12 (s, 2H, H-2″), thiophene-H, [6.54 (d, J = 2.8 Hz,
1H, H-3′), 6.91 (dd, J = 2.9, 2.8 Hz, 1H, H-4′), 7.09 (d,
J = 2.9 Hz, 1H, H-5′)], Ar–H [7.23 (br s, 1H, H-2‴), 7.33
(d, J=8.0 Hz, 1H, H-5‴), 7.38 (d, J=8.0 Hz, 1H, H-6‴)],
7.90 (s, 1H, NH); 13C-NMR (125 MHz, CDCl3): δ 14.6
(CH3), 19.3 (CH3), 21.3 (CH3), 31.4 (C-6′), 35.4 (C-2″),
46.1 (CH2), thiophene-C [126.4 (C-4′), 130.0 (C-3′),
134.9 (C-5′), 138.7 (C-1′)], Ar–C [125.2 (C-5‴), 126.2
(C-6‴), 127.2 (C-2‴), 128.3 (C-3‴), 128.7 (C-4‴), 137.1
(C-1‴)], 151.2 (C-5), 153.7 (C-3), 168.5 (C-1″); HR-EI-
MS (m/z): 386.1227 [M]+ calculated for C19H22S2N4O;
386.1235.
N‑(2,5‑dimethylphenyl)‑2‑(4‑ethyl‑5‑(thiophen‑2‑ylmethyl)‑
4H‑1,2,4‑triazol‑3‑ylthio)acetamide (9c)
Amorphous powder; yield: 69%; M.P.: 126–127 °C; IR
(KBr) vmax: 3025, 2910, 1685, 1580, 1540 cm−1; 1H-NMR
(500 MHz, CDCl3): δ 1.08 (t, J=6.5 Hz, 3H, CH3–CH2–N),
2.15 (s, 3H, CH3), 2.29 (s, 3H, CH3), 3.85 (q, J=6.5 Hz, 2H,
CH3–CH2–N), 4.01 (s, 2H, H-6′), 4.12 (s, 2H, H-2″), thio-
phene-H [6.52 (d, J=3.0 Hz, 1H, H-3′), 6.80 (dd, J=3.5,
3.0 Hz, 1H, H-4′), 7.15 (d, J = 3.5 Hz, 1H, H-5′)], Ar–H,
[7.01 (br s, 1H, H-6‴), 6.97 (d, J = 7.8 Hz, 1H, H-3‴),
7.37 (d, J=7.8 Hz, 1H, H-4‴), 7.79 (s, 1H, NH); 13C-NMR
(125 MHz, CDCl3): δ 13.6 (CH3), 16.2 (CH3), 20.1 (CH3),
30.1 (C-6′), 35.3 (C-2″), 44.5 (CH2), 126.6 (C-4′), 130.0
(C-3′), 134.9 (C-5′), 136.1 (C-2′), Ar–C [125.0 (C-3‴),
125.2 (C-4‴), 126.2 (C-6‴), 126.8 (C-2‴), 129.0 (C-5‴),
137.3 (C-1‴)], 150.5 (C-5), 154.6 (C-3), 167.3 (C-1″); HR-
EI-MS (m/z): 386.1227 [M]+ calculated for C19H22S2N4O;
386.1235.
N‑(3,5‑Dimethylphenyl)‑2‑(4‑ethyl‑5‑(thiophen‑2‑ylmethyl)‑
4H‑1,2,4‑triazol‑3‑ylthio)acetamide (9f)
Amorphous powder; yield: 67%; M.P.: 127–129 °C; IR
1
(KBr) vmax: 3020, 2925, 1697, 1591, 1530 cm−1; H-
NMR (500 MHz, CDCl3): δ 1.04 (t, J = 6.5 Hz, 3H,
CH3–CH2–N), 1.94 (s, 3H, CH3), 2.05 (s, 3H, CH3), 3.83
(q, J = 6.5 Hz, 2H, CH3–CH2–N), 4.01 (s, 2H, H-6′), 4.12
(s, 2H, H-2″), thiophene-H, 6.62 [(d, J=2.8 Hz, 1H, H-3′),
6.85 (dd, J = 3.0, 2.8 Hz, 1H, H-4′), 7.10 (d, J = 3.0 Hz,
1H, H-5′)], Ar–H [7.23 (br s, 1H, H-2‴), 7.33 (br s, 1H,
H-4‴), 7.35 (br s, 1H, H-6‴)], 7.98 (s, 1H, NH); 13C-
NMR (125 MHz, CDCl3): δ 14.6 (CH3), 16.3 (CH3), 20.3
(CH3), 31.4 (C-6′), 33.2 (C-2″), 45.1 (CH2), thiophene-C
[126.4 (C-4′), 130.0 (C-3′), 134.9 (C-5′), 138.7 (C-2′)],
Ar–C [125.2 (C-2‴), 126.2 (C-4‴), 127.2 (C-6‴), 128.3
(C-3‴), 130.7 (C-5‴), 137.1 (C-1‴)], 151.2 (C-5), 153.7
(C-3), 168.5 (C-1″); HR-EI-MS (m/z): 386.1227 [M]+ cal-
culated for C19H22S2N4O; 386.1235.
N‑(2,6‑dimethylphenyl)‑2‑(4‑ethyl‑5‑(thiophen‑2‑ylmethyl)‑
4H‑1,2,4‑triazol‑3‑ylthio)acetamide (9d)
Amorphous powder; Yield: 62%; M.P.: 151–153 °C;
IR (KBr) vmax: 3025, 2915, 1689, 1570, 1540 cm−1;
1H-NMR (500 MHz, CDCl3): δ 1.05 (t, J = 6.5 Hz, 3H,
CH3–CH2–N), 1.82 (s, 3H, CH3), 1.93 (s, 3H, CH3), 3.84
(q, J = 6.5 Hz, 2H, CH3–CH2–N), 4.00 (s, 2H, H-6′), 4.10
1 3