Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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. HPLC of Formula: C7H10N2O2
To an oven- dried three-neck reaction flask charged with a magnetic stir bar, an internal thermometer at rt under argon was added ethyl 4-methyl-lH-imidazole-5- carboxylate (2.20 g, 14.3 mmol) and anhydrous DMF (71 mL). The yellow solution was cooled to -20C using a dry ice and EtOAc bath. Lithium hexamethyldisilane (1.0M in TetaF, 15.7 mL, 15.7 mmol) was then added dropwise via an addition funnel while maintaining the internal temperature below -12C. To the solution was then added o-(diphenylphosphinyl)- hydroxylamine (4.00 g, 17.1 mmol) in two portions while maintaining the internal temperature at O0C. The resulting white suspension was diluted by the addition of DMF (15 mL) and stirred at rt overnight. The white suspension was quenched with water (5 mL) and the solvent was removed under vacuum. The resulting yellow solid was extracted with CH2Cl2 (50 mL), EtOAc (100 mL) and then the organic extracts were combined and concentrated by rotary evaporation to a brown solid. It was purified by flash column chromatography (80 g pre-packed silica gel column, gradient elution with CH2Cl2, to CH2Cl2:Me0H, 4:96) to give 1.00 g (41%) of the title compound as a white solid. 1H NMR (CDCl3) 7.59 (s, I H), 5.32 (br s, 2H), 4.36 (q, J= 7.1 Hz, 2H), 2.45 (s, 3H), 1.40 (t, J= 7.0 Hz, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51605-32-4, its application will become more common.
Reference:
Patent; CYTOVIA, INC.; WO2008/57402; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem