In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4592-94-3
General procedure: To a solution of 0.45 g of 3-(4-bromophenyl)-3-oxopropanenitrile (6a, 2.0 mmol) in 25 mL of ethanol, 0.165 g of benzothiazolylhydrazine (5a, 1.0 mmol) and 0.058 g of propionaldehyde (8a, 1.0 mmol) were added along with 2 drops of conc. HCl. The reaction mixture was heated to reflux for 45 minutes until the formation of a solid product in the reaction mixture. The hot reaction mixture was filtered at the vacuum pump and washed with hot ethanol to afford the pure compound 7a. All other compounds (7b-i) were synthesized according to the procedure mentioned for 7a using heteroarylhydrazines (5a-c), different 3-aryl-3-oxopropanenitriles (6a-d) and aldehydes (8a-d). 1-(Benzo[d]thiazol-2-yl)-4,7-dihydro-4-ethyl-3,6-di(4-bromophenyl)-1H-pyrazolo[3,4-b]pyridine-5-nitrile (7a). Yield 62%; M.p. 240-245 C; IR (KBr, cm-1): 2208 (CN), 3340 (N-H); 1H NMR (400 MHz, CDCl3): delta 0.87-0.90 (t, 3H, CH3, J 6.8 Hz), 1.71-1.89 (m, 2H, CH2), 4.44-4.46 (t, 1H, 4-H, J 4 Hz), 7.38-7.42 (m, 1H, 6?-H), 7.48-7.51 (m, 1H, 5′-H), 7.62-7.69 (m, 6H, Ph-H), 7.72-7.74 (m, 2H, 2??-H), 7.78-7.80 (d, 1H, 7′-H, J 8.0 Hz), 7.86-7.88 (d, 1H, 4′-H, J 8.0 Hz), 9.1 (s, 1H, exchangeable with D2O, 7-H); 13C NMR (75 MHz, CDCl3): delta 8.8, 28.2, 36.6, 84.7, 99.5, 121.7, 121.9, 123.4, 125.1, 125.4, 126.8, 128.7, 129.3, 130.9, 131.5, 132.0, 132.6, 139.9, 148.4, 150.3, 160.7; MS: m/z 615.97 [M+1]+, 617.97 [M+1+2]+, 619.97 [M+1+4]+, (1:2:1); Elemental analysis: Calcd. for C28H19Br2N5S: C, 54.47; H, 3.10; N, 11.34; Found: C, 53.35; H, 2.63; N, 11.12.
The synthetic route of 4592-94-3 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Aggarwal, Ranjana; Kumar, Suresh; Singh, Gulshan; Synthetic Communications; vol. 49; 7; (2019); p. 973 – 985;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts