[Synthesis]
Under argon protection, 4-tert-butylbenzoyl chloride (10 mmol, 1.97 g) was dissolved in acetone (20 mL), sodium thiocyanate (10 mmol, 0.81 g) was added, and the reaction was stirred for 2 hours. Subsequently, the above reaction mixture was slowly added dropwise to a solution of 1,4-phenylenediamine (20 mmol, 2.16 g) in acetone (50 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 36 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue obtained was dissolved in dichloromethane, filtered to remove insoluble material and the filtrate was concentrated again. Purification was carried out by silica gel column chromatography, eluting using a solvent mixture of ethyl acetate-petroleum ether. The target fraction was collected, concentrated and ground with ether to afford analytically pure N-((4-aminophenyl)thiocarbamoyl)-4-(tert-butyl)benzamide in a yield of 2.45 g (75% yield). The product characterization data were as follows: melting point 189-191°C; 1H-NMR (CDCl3) δ 1.36 (s, 9H), 6.81 (m, 2H), 7.47 (m, 2H), 7.54 (m, 2H), 7.81 (m, 2H), 9.05 (s, 1H), 12.41 (s, 1H); MS (ES+) m/z 350 [M + Na]+; elemental analysis calculated value C18H21N3ONaS 350.1300, measured value 350.1303. |