2-Pyridinecarbothioamide

General procedure: a. Ground phosphoruspentasulfide (115 g, 0.5 mol) was added to asolution of 4-cyanopyridine (52 g, 0.5 mol) in 250 mLof 20percent ammonium in methanol under vigorous stirringmaintaining the reaction mixture temperature below35–40°C. The reaction mixture was kept at roomtemperature for 12 h, After the reactionended, 150 mL of water was added and the mixturewas heated up to 70–75°C by water bath till the gasevolution stopped. After cooling the precipitate wasfiltered off, washed with water, and dried. Yield 89percent(61.8 g), Rf 0.45, mp 137° (136–137° [21]). Found, percent: 52.09; H 4.31; N 20.30; S 23.30. C6H6N2S.Calculated, percent: 52.15; H 4.38; N 20.27; S 23.20.General procedure: The corresponding nitrile (100 mmol) prepared as described previouslyGeneral procedure: Benzonitrile 1a (1 mmol), Na2S*9H2O (1.2 mmol) and DMF (1 mL) were added into a 10 mL bottle. The reactor was placed in a heating magnetic stirrer at 130 °C. After 2.5 h, by adding about 3 mL H2O after the reaction to disperse the solid product, the reaction mixture was extracted with EtOAc (3 x 3 mL), and the mixture was purified by column chromatography.General procedure: In a typical reaction a solution of amide (1 mmol), rhodanine (1.2 mmol) and Morpholine (1.2 mmol) in EtOH/water (2 + 2 ml) were refluxed at 80-90 °C till completion using 40 mg of MCM-41 catalyst. The completion of the reaction was indicated by the disappearance of the starting material in thin layer chromatography. After completion of the reaction the solvent was evaporated in a rotary evaporator and the crude product was taken in dichloromethane and filtered to separate the products as filtrate from the catalyst (residue). Then the crude product was purified by silica gel column chromatography where the compound (5) came out from the column with 25percentEtOAc/75percent petroleum ether, but thioamide (4) came out with 65percentEtOAc/35percent petroleum ether making their separation easy. The thioamides (4) were characterized by IR,

Molecular Weight:138.19
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:138.02516937
Monoisotopic Mass:138.02516937
Topological Polar Surface Area:71
Heavy Atom Count:9
Complexity:114
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes