Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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. category: imidazoles-derivatives
Triphenylphosphine (47.64 g, 181.64 mmol) and diisopropyl azodicarboxylate (36.73 g, 181.64 mmol) were dissolved in tetrahydrofuran (120.00 mL) at 0 C under a nitrogen atmosphere, followed by sequential addition of compound 1 (10.00 g, 90.82 mmol) and n-propanol (10.91 g, 181.64 mmol). The mixture was warmed to 25 C and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, dilute hydrochloric acid (1 M) was added to the mixture to adjust to pH = 1 and extracted with ethyl acetate (50 mL × 3). The aqueous phase was adjusted to pH = 13 with sodium hydroxide (1M) and extracted with ethyl acetate (50 mL × 4). The organic phases were combined, washed with saturated brine (50 mL 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (petroleum ether: ethyl acetate = 20:1-5:1) to obtain the title compound BB-3H-2 ((12.00 g, pale-yellow oily liquid, yield: 27.60%). 1H NMR (400MHz,CDCl3) delta: 9.81 (s, 1H), 7.50 (s, 1H), 4.19 (t, J = 7.1 Hz, 2H), 2.49 (s, 3H), 1.98- 1.74 (m, 2H), 0.89 (t, J = 7.5 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 68282-53-1, its application will become more common.
Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem