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

General procedure: 5.1.1 General procedure: A mixture of benzoic acid (5.0 g, 40.94 mmol), thiosemicarbazide(3.67 g, 40.26 mmol) and phosphorus oxychloride(9.25 mL) was refluxed under continuous stirring. Thereaction mixture was cooled to room temperature and wasrefluxed further for 2 h after the addition of water (55 mL).After cooling, the mixture was basified to pH 9 by dropwise addition of 50percent sodium hydroxide solution. The solidso obtained was filtered, dried and recrystallised fromethanol to afford 4a (5.65 g, 78percent), m.p. 221–223 °C (Lit.224–225 °C) (Guan et al. 2014). The same procedure was performed with 2-chloro benzoicacid with a reflux of 6 h to yield 4b (5.81 g, 86percent), m.p.220–222 °C (Lit. 220–221 °C).General procedure: 4.2.2.1. 5-(4-Fluorophenyl)-1, 3, 4-thiadiazol-2-amine (2b). A mixture of 4-fluoro benzoic acid (5.0 g, 35.70 mmol), thiosemicarbazide (3.25 g, 35.70 mmol) and POClGeneral procedure: Compounds 1{5 (1 mmol) were dissolved in ethanol and ethanolic ferric chloride solution (4 mmol) wasadded. The reaction mixtures were heated under reux for 16{20 h. The mixtures were neutralized usingammonia solution, ltered and washed with water, dried, and crystallized from ethanol to obtain compounds 6-10.General procedure: A mixture of aldehydes (1 mmol), thiosemicarbazide (1 mmol) in ethanol (10 mL) and tert-butyl hydroperoxide (TBHP, 70percent aqueous solution) (1 mmol) was stirred at room temperature for 4h. The progress of the reaction was monitored by TLC using hexane/ EtOAc as the mobile phase. After the completion of the reaction, ethanol was evaporated under vacuum to obtain a solid residue. To this solid residue, ethyl acetate (10 ml) and water (10 ml) were added followed by saturated sodium bicarbonate solution (10 mL). Separated organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum to obtain the product, which was further purified using silica gel column chromatography (hexane/ethyl acetate).

Molecular Weight:211.67
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:210.9970961
Monoisotopic Mass:210.9970961
Topological Polar Surface Area:80
Heavy Atom Count:13
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes