Some common heterocyclic compound, 7357-70-2, name is 2-Cyanothioacetamide, molecular formula is C3H4N2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 7357-70-2
To a suspension of 3-(1,2-dimethyl-1H-imidazol-5-yl)-1-(thiazol-2- yl)prop-2-en-1-one (0.31 mmol, 72 mg) and 2-cyanothioacetamide (0.93 mmol, 93 mg, 3.0 equiv.) in EtOH (1.5 mL), a few drops of piperidine were added. After being stirred at 80oC for 2 h, EtOH was evaporated and crude product was redissolved in CH3CN. (0383) Butyl(chloromethyl)sulfane (0.62 mmol, 85.5 mg) and Et3N (0.93 mmol, 94.1 mg, 130 muL) were then added and the reaction mixture was stirred at 80C for 20 min. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and aqueous layer was extracted twice with EtOAc. The combined extractions were washed with saturated NaCl solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography to give 99 mg of designed product (77%). 1H NMR (400 MHz, CDCl3) delta 7.96 (d, J = 3.1 Hz, 1H), 7.85 (s, 1H), 7.56 (d, J = 3.1 Hz, 1H), 7.37 (s, 1H), 4.49 (s, 2H), 3.60 (s, 3H), 2.72 (t, J = 7.4 Hz, 2H), 2.48 (s, 3H), 1.62 (p, J = 7.3 Hz, 2H), 1.40 (h, J = 7.3 Hz, 2H), 0.90 (t, J = 7.3 Hz, 3H). ESI- MS (m/z): 416.6 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7357-70-2, its application will become more common.
Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER; UNIVERSITY OF IOWA RESEARCH FOUNDATION; MARKOWITZ, Sanford; READY, Joseph; PIEPER, Andrew; (168 pag.)WO2018/17582; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts