Electric Literature 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: A mixture of the corresponding 2-amino-4-arylimidazole 1(1.0 mmol), aromatic aldehyde 2 (2.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products 16were filtered off and crystallized from iPrOH. 16a: yellowpowder, 30%, mp 239-240 C; 1H NMR (200 MHz, DMSO-d6)delta 9.32 (s, 1H, CHazomethine), 8.12 (d, J = 6.7 Hz, 2, Ar),7.67-7.45 (m, 5, Ar), 7.27-7.04 (m, 10, C5NH2, Ar), 5.15(s, J = 6.7 Hz, 1H, C7H), 4.05-3.84 (m, 2, 23), 1.01(s, J = 7.0, 3H, 2CH3); 13C NMR (125 MHz, DMSO-d6) delta178.7 (CO), 134.5, 133.3, 130.2, 129.6, 128.7, 128.6, 128.3, 127.8, 127.2, 127.0, 126.4, 125.8, 125.5, 116.7, 93.4, 58.9, 43.4,14.7; MS (m/z) (%): 448 ([M+?], 100; anal. calcd. forC28H24N4O2 (448.19) C, 74.98; H, 5.39; N, 12.49; found: ,75.12; H, 4.89; N, 11.37.
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