Synthetic Route of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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.
General procedure: An equimolar mixture (1.0 mmol) of thecorresponding 2-amino-4-arylimidazole 1, aromatic aldehyde 2and Meldrum?s acid 3 was refluxed in iPrOH (3 mL) for3-5 min. After cooling, the solid products 4 were filtered off,washed with iPrOH and dried on air. 4a: colourless solid, 77%;mp 243-245 C; IR (KBr, cm-1) nu: 3404-2800 (NH2, NH, OH),1684 (C=O); 1H NMR (200 MHz, DMSO-d6) delta 12.27 (br s, 2H,NH, OH), 7.61-7.49 (m, 2H, Harom), 7.48-7.31 (m, 5H, Harom),7.27-7.01 (m, 5H, NH2,, Harom), 5.48 (s, 1H, CH), 1.51 (s, 6H,CH3); 13C NMR (125 MHz, CDCl3) delta 166.8 (C=O), 146.6(C-OH), 144.0, 129.4, 128.9, 128.4, 128.3, 127.5, 127.4, 127.2,125.9, 121.1, 100.6, 76.0 (C=COH), 35.1 (CH), 26.4 (CH3),25.9 (CH3); MS (m/z) (%): 289 (76), (391 [M+?] – 44 -58), 247(53), 159 (36), 104 (19), 77 (8), 44 (39), 43 (100); anal. calcdfor C22H21N3O4 (391.5) C, 67.52; H, 5.37; N, 10.74; found: C,68.77; H, 5.93; N, 10.79.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.
Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem