Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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. 7098-07-9
Intermediate la 1 -Ethyl-5 -iodo- 1 H-imidazole In a 100 mL three-necked flask, TMEDA (2.86 g, 3.72 ml, 24.7 mmol, Eq: 2.37) was combined with pentane (10 ml) to give a colorless solution. N-BuLi 1.6M in hexane (15.6 ml, 25.0 mmol, Eq: 2.4), followed by 1 -ethyl- 1 H-imidazole (1 g, 10.4 mmol, Eq: 1.00) were added dropwise at -25¡ãC for 30 min. The reaction mixture was stirred at RT for 1 h (light yellow suspension). Afterwards, the suspension was cooled to -65¡ãC and THF anhydrous (30 ml) was added (-65¡ãC to -48¡ãC). A solution of iodine (3.83 g, 15.1 mmol, Eq: 1.45) in THF anhydrous (20 ml) was added dropwise to the reaction mixture (internal temperature remained below -55¡ãC) => brown suspension. Stirring was continued as the reaction was gradually warmed to 0¡ãC during 1.3 hours (brown milky solution). Eventually, the reaction was quenched by adding 4 mL of methanol. Work up: The reaction mixture was poured into 50 mL sat. Na2S03 and extracted with EtOAc (2 x 100 mL). The organic layers were combined, washed with brine, dried over Na2S04, and concentrated i. V. Purification : The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 100percent EtOAc in heptane) to provide in the more polar fractions 417 mg of the desired title compound as yellow oil. MS (ESI): 222.9 [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 7098-07-9, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans, P.; MAYWEG, Alexander, V.; MOHR, Peter; TAN, Xuefei; WO2013/120771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem