The precipitation of hydrazide 3 was filtered, dried, and crystallized from ethanol. Yield: 91.4 %, mp: 196–198 °C (dec.). Analysis for C16H15N5OS (325.39); calculated: C, 59.06; H, 4.65; N, 21.52; S, 9.82; found: C, 59.10; H, 4.63; N, 21.49; S, 9.78. IR (KBr), ν (cm−1): 3105 (CH Foretinib aromatic), 2980, 1423 (CH aliphatic), 1698 (C=O),

1611 (C=N), 1522 (C–N), 699 (C–S). 1H NMR (DMSO-d 6) δ (ppm): 3.91 (s, 2H, CH2), 4.31 (s, 2H, NH2), 7.31–7.57 (m, 10H, 10ArH), 9.40 (brs, 1H, NH). Derivatives of thiosemicarbazide (4a–l) General method (for compounds 4a–l) A mixture of 3.25 g (10 mmol) of hydrazide (3) and 10 mmol appropriate isothiocyanate was heated in an oil bath at 50–110 °C for 8–20 h. The product was washed with learn more diethyl ether to remove unreacted isothiocyanate. Then it was filtered, dried, and crystallized from ethanol 4a–c, d, g–l, butanol 4e, or methanol 4f. Method B (for compounds 4a, c, d) 10 mmol of appropriate isothiocyanate

was added to 3.25 g (10 mmol) of hydrazide 3 in 10 mL of anhydrous diethyl ether. The mixture, placed in a conical bulb, was mixed for 5 min and left in room temperature for 24 h. The precipitation of thiosemicarbazide 4a, c, d was filtered, dried, and crystallized from ethanol. The obtained compounds had the same melting points as the compounds obtained by the general method. 4-Ethyl-1-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl thiosemicarbazide (4a) Yield: 94.0 %. Temperature of reaction: 70 °C

for 8 h, mp: 205–207 °C (dec.). Analysis for C19H20N6OS2 (412.53); selleck compound calculated: C, 55.32; H, 4.89; N, 20.37; S, 15.54; found: C, 55.23; H, 4.88; N, 20.43; S, 15.59. IR (KBr), ν (cm−1): 3199 (NH), 3101 (CH aromatic), 2974, 1453, 741 (CH aliphatic), 1699 (C=O), 1607 (C=N), 1519 (C–N), 1329 (C=S), 691 (C–S). 1H NMR (DMSO-d 6) δ (ppm): 1.12 (t, J = 9 Hz, 3H, CH3), 3.51–3.60 (q, J = 7.5 Hz, J = 7.5 Hz, 2H, CH2), 3.90 (s, 2H, CH2), 7.34–7.57 (m, 10H, 10ArH), 8.32, 9.33, 10.25 (3brs, 3H, 3NH). 13C NMR δ (ppm): 14.61 (CH3), 30.75 (–S–CH2–), 33.90 (–CH2–CH3), 126.42, 127.68, selleck 127.95, 128.79, 130.07, 130.11 (10CH aromatic), 130.33, 133.65 (2C aromatic), 152.08 (C–S), 154.59 (C-3 triazole), 166.82 (C=O), 181.23 (C=S). MS m/z (%): 412 (M+, 2), 397 (3), 335 (2), 325 (5), 294 (26), 253 (61), 252 (100), 194 (21), 180 (20), 149 (20), 118 (23), 104 (25), 91 (44), 77 (79). 4-Allyl-1-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl thiosemicarbazide (4b) Yield: 90.7 %. Temperature of reaction: 55 °C for 12 h, mp: 192–194 °C (dec.). Analysis for C20H20N6OS2 (424.54); calculated: C, 56.58; H, 4.75; N, 19.79; S, 15.10; found: C, 56.53; H, 4.76; N, 19.81; S, 15.14.