2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE

General procedure: A stirring mixture of benzoic acid (0.2442 g, 2.0 mmol), thiosemicarbazide (0.1823 g, 2.0 mmol) and POCl3 (1.2 ml) was heated at 80 General procedure: 5.1.1 General procedure: A stirring mixture of benzoic acid (7.32 g, 60 mmol), N-aminothiourea(6.38 g, 70 mmol) and POCl3 (20 ml) washeated at 75 °C for 0.5 h. After cooling down to room temperature, water was added. The reaction mixture was refluxedfor 4 h. After cooling, the mixture was basified to pH8 by the drop-wise addition of 50percent NaOH solution understirring. The precipitate was filtered and re-crystallized from ethanolp-Anisic acid (3.04 g, 20 mmol) and thiosemicarbazide (1.82 g, 20 mmol) were dissolved in 30 mL of phosphorus oxychloride, thereaction mixture was refluxed at 85 °C for 10 h. After the reactionfinished, the mixture was poured into ice water slowly and thensaturate NaOH solution was added to adjust the pH value to 8.0under vigorous stirring. The mixture was extracted with ethyl acetatethree times, the organic layer was washed with brine anddried over anhydrous sodium sulfate. After solvent evaporation, thecrude product was purified by recrystallization from anhydrousethanol to get 3.15 g white powder, yield: 76.09percent. Melting point:188.1-189.5 °C. FT-IR (KBr, Disc, cm1): 3409.28 (m, ν NH2), 3377.72(m, ν NH2), 3304.97 (w), 3105.35 (m), 1647.15 (m), 1608.48 (m, ν CN), 1578.80 (w), 1511.49 (s, ν benzene), 1465.51(s), 1304.97 (w), 1267.34(w), 1246.65 (s, ν OCH3), 1174.54 (m, ν OCH3), 1128.97 (w), 1052.67 (w), 1031.98 (m), 978.88 (w), 829.22 (m), 658.86 (w), 520.48 (w). 1HNMR (DMSO-d6, 400 MHz, ppm) δ: 7.69-7.67 (d, J= 8.0 Hz, 2H), 7.28 (s, 2H, NH2), 7.03-7.01 (d, J =8.0 Hz, 2H), 3.80 (s, 3H, OCH3). 13CNMR (100 MHz, DMSO) δ 167.85, 160.24, 156.25, 127.77, 123.61, 144.46, 55.27. MS (ESI) m/z: found, [M+H]+, 208.0542; molecularformula C9H9N3OS requires [M+H]+, 208.0544.General procedure: A mixture ofappropriate 4-n-alkoxybenzoic acid (10 mmol) and (0.91 g, 10 mmol) of thiosemicarbazidewith 5 mL of phosphorus oxychloride was refluxed gently for 5 hr. After cooling 50 mL of water was added, the mixture was then refluxed for 7 hr and filtered, neutralizedwith potassium hydroxide. The precipitate was washed with water and recrystallized fromethanol-water to give titled compound [III]n.

Molecular Weight:207.25
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:207.04663309
Monoisotopic Mass:207.04663309
Topological Polar Surface Area:89.3
Heavy Atom Count:14
Complexity:185
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes