1
Yield 73 %. FT-IR (υmax, cm-1): 3210 (NH2), 3051 (aromatic CH), 1583 (C=N). H
NMR (DMSO-d6, δ ppm): 2.63 (2H, d, J= 4.0 Hz, CH2), 2.79 (2H, s, CH2), 3.42-3.47 (4H, m,
2CH2), 3.74-3.80 (4H, m, 2CH2), 4.41 (2H, d, J= 8.0 Hz, CH2), 7.35-7.38 (2H, m, NH2), 7.52-
7.55 (1H, m, arH), 7.73 (1H, s, arH), 7.89 (1H, d, J= 8.0 Hz, arH), 8.26 (1H, d, J= 8.0 Hz,
arH), 9.03 (1H, s, CH). 13C NMR (DMSO-d6, δ ppm): 28.33 (CH2), 48.35 (CH2), 51.13 (CH2),
54.39 (CH2), 56.52 (CH2), 61.58 (CH2), 61.84 (CH2), arC: [124.33 (CH), 124.58 (CH), 129.10
(C), 132.53 (CH), 134.89 (CH), 135.38 (CH)], 146.66 (thiadiazole C-3), 147.96 (triazole C-3),
150.37 (thiadiazole C-5), 152.44 (triazole C-5). EI MS m/z (%): 449.70 ([M+2]+, 51), 425.32
([M-Na+1]+, 34), 400.01 (100). Elemental analysis for C17H21N9S3 calculated (%), C, 45.62;
H, 4.73; N, 28.16, found (%), C, 45.59; H, 4.75; N, 28.09.
4.6.10. 2-[2-(5-Amino-1,3,4-thiadiazol-2-yl)ethyl]-5-(morpholin-4-ylmethyl)-4-{[pyridin-
4-ylmethylene]amino}-2,4-dihydro-3H-1,2,4-triazol-3-thione (8d)
1
Yield 81 %. FT-IR (υmax, cm-1): 3310 (NH2), 3067 (aromatic CH), 1582 (C=N). H
NMR (DMSO-d6, δ ppm): 1.76 (4H, s, 2CH2), 2.15 (4H, s, 2CH2), 3.39 (4H, s, 2CH2), 3.75
(2H, d, J= 8.0 Hz, CH2), 5.46 (2H, s, NH2), 7.63-7.65 (2H, m, arH), 7.97-7.99 (2H, m, arH),
10.90 (1H, s, CH). 13C NMR (DMSO-d6, δ ppm): 19.06 (CH2), 24.48 (CH2), 30.63 (CH2),
40.63 (CH2), 42.75 (CH2), 63.05 (CH2), 65.37 (CH2), 111.93 (CH), arC: [110.75 (C), 118.94
(CH), 119.04 (CH), 121.57 (CH), 123.80 (CH)], 145.41 (thiadiazole C-3), 153.56 (triazole C-
3), 159.64 (thiadiazole C-5), 178.54 (triazole C-5). EI MS m/z (%): 449.53 ([M+2]+, 49),
423.20 ([M-Na+3]+, 42), 405.22 (100). Elemental analysis for C17H21N9S3 calculated (%), C,
45.62; H, 4.73; N, 28.16, found (%), C, 45.60; H, 4.76; N, 28.12.
4.6.11.
2-[2-(5-Amino-1,3,4-thiadiazol-2-yl)ethyl]-4-{[(2,6-dichlorophenyl)methylene]
amino}-5-(thiomorpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-thione (8e)
Yield 79 %, m.p: 152-154 °C. FT-IR (υmax, cm-1): 3215 (NH2), 3057 (aromatic CH),
1
1581 (C=N). H NMR (DMSO-d6, δ ppm): 1.10-1.14 (2H, m, CH2), 2.59-2.61 (2H, m, CH2),
2.70 (2H, d, J= 8.0 Hz, CH2), 3.32 (2H, s, CH2), 3.63 (2H, s, CH2), 3.77 (2H, d, J= 8.0 Hz,
CH2), 4.38-4.41 (2H, m, CH2), 5.66 (2H, s, NH2), 7.23-7.45 (3H, m, arH), 8.84 (1H, s, CH).
13C NMR (DMSO-d6, δ ppm): 48.31 (CH2), 51.43 (CH2), 54.46 (CH2), 58.72 (CH2), 61.74
(CH2), 63.68 (CH2), 66.82 (CH2), arC: [129.36 (CH), 129.42 (CH), 131.61 (C), 132.29 (C),
132.33 (2CH), 133.61 (C)], 147.98 (thiadiazole C-3), 154.49 (triazole C-3), 165.84
(thiadiazole C-5), 169.21 (triazole C-5). EI MS m/z (%): 533.53 ([M+H2O]+, 77), 500.11