Reference of 1792-40-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
To a solution of 5-nitrobenzimidazole (1.0 G, 5.6 MMOL) in acetone (50 mL) was added potassium carbonate (1.0 g), followed by alkyl halide (1.2-1. 5 equivalents). The mixture was stirred under nitrogen at rt, then partitioned between ethyl acetate and water after TLC showed completion of the reaction. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a mixture of 1-ALKYL- 5-NITRO-2-METHYLBENZIMIDAZOLE and 1-alkyl-6-nitro-2-methylbenzimidazole, which were dissolved in ethanol-THF (100 mL, 2: 1) and hydrogenated over 5% Pd-C under atmosphere pressure for 8h. After filtration through celte, the filtrate was evaporated to give a yellow solid that was separated with flash chromatography (Methanol-DCM gradient elution). 1-Alkyl-5-aminobenzimidazole and 1-alkyl-6-aminobenzimidazole were obtained as yellow solid or thick syrup.; 5-Amino-1, 2-DIMETHYLBENZIMIDAZOLE (XDS01191B, XDS02082B): Yellow solid, mp 126-127C (LIT. 128C, [23] ). TLC single spot at Rf 0.30 (5% methanol/DCM) ;’H NMR (270 MHz, DMSO): 6 7.08 (1H, d, J = 8.7 Hz, 7-H), 7.65 (1H, d, J = 1.5 Hz, 4-H), 6.50 (1H, dd, J = 8.7, 1.5 Hz, 6-H), 4.63 (2H, broad, NH2), 3.58 (3H, s, NCH3), 2.39 (3H, s, CH3). 6-Amino-1, 2-DIMETHYLBENZIMIDAZOLE (XDS01191A, XDS02082A): Yellow solid. TLC single spot at Rf 0.33 (5% methanol/DCM) ;’H NMR (270 MHz, DMSO): 6 7. 13 (1H, d, J = 8.4 Hz, 4-H), 6.48 (1H, d, J = 2. 0 Hz, 7-H), 6.43 (1H, dd, J = 8.4, 2.0 Hz, 5-H), 4.83 (2H, broad, NH2), 3.53 (3H, s, NCH3), 2.39 (3H, s, CH3).
The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.
Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
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