5,6-Dimethylbenzimidazole

light beige powder

Solid

5,6-dimethylbenzimidazole is a dimethylbenzimidazole carrying methyl substituents at positions 5 and 6. It has a role as an Escherichia coli metabolite and a human metabolite.

General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt percent, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 µL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 µM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10percent MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99percent). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction.General procedure: To a 10mL three-necked round bottle was charged with 1a (0.54 g, 5 mmol), imidazolium chloride (0.09 g, 0.5 mmol) and N, N-dimethylformamide 2 mL. The resulting solution was warmed to120 °C and stirred at this temperature for 6 h. When the reaction was completed, 25 mL water was added and the resulting mixture was extracted with 25 mL ethyl acetate twice. The combined organic layer was successively washed with H2O (50 mL) and then brine (50 mL), then dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate or recrystallized from petroleum ether/EA to give the title products.General procedure: A mixture of 1a (1b-1n, 0.4 mmol) and PhSiH3 (98 mL, 1.6 mmol)in N, N-dimethylformamide 2a (2b-2c, 1 mL) was stirred at 120 °C for 12 h. When the reaction was completed, the resulting mixture was extracted with ethyl acetate three times. The combined organic layer was washed by NaCl aqueous solution and dried over anhydrous Na2SO4, after which the solvent was removed under reduced pressure. The residue was purified by column chromatography onsilica gel with petroleum ether and ethyl acetate (6:1-1:2) to give the corresponding product 3a (3b-3p).1-(N-(Ribityl)), 2-diamino-4, 5-dimethylbenzene 3 (200mg, 0.74mmol) was dissolved in water (100mL), and the resulting solution stirred vigorously at ambient temperature. Compressed air was continuously bubbled through the solution. After 96h, the solution was extracted with EtOAc (3×30mL), and the aqueous fraction lyophilised to furnish starting material 3 (174mg, 0.64mmol, 87percent). Combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (50mL) and brine (2×50mL), before drying over MgSO

Molecular Weight:146.19
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:146.084398327
Monoisotopic Mass:146.084398327
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes