Extracurricular laboratory: Synthetic route of Methyl 1H-benzo[d]imidazole-4-carboxylate

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Methyl 1H-benzo[d]imidazole-4-carboxylate

Methyl 1H-benzo[d]imidazole-4-carboxylate (0.504 g, 2.861 mmol) was dissolved in THF/dioxane (3:2, 50 mL). A 1.0 M solution LiAlH4 in THF (3.00 mL, 3.00 mmol) was added slowly and the reaction was left to stir for 1 hour. The reaction was quenched by successive addition of water (114 muL), 15% NaOH (114 muL) and water (342 muL). The suspension was stirred for 5 minutes and Na2SO4 (3.0 g) was added and the stirring was continued for 10 minutes. The suspension was filtered and the filter cake washed with THF (2 × 15 mL). The combined filtrates were evaporated under reduced pressure to give the title compound (0.356 g, 84%) as a white solid. mp. 159 – 161 C. 1H NMR (300 MHz, CD3OD) delta 8.13 (s, 1H), 7.51 (dd, J = 7.4, 1.7 Hz, 1H), 7.26 (dd, J = 7.3, 1.7 Hz, 1H), 7.21 (dd, J = 7.3, 7.4 Hz, 1H), 5.07 (br s, 2H), 4.98 (s, 3H). 13C NMR (75 MHz, CD3OD) delta 142.2, 139.2, 136.0, 129.5, 123.5, 121.7, 115.5, 61.8.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem