5,6-DICHLORO-2-METHYLBENZIMIDAZOLE

General procedure: To a mixture of o-aromatic diamines (200 mg, 1.85 mmol) and 1, 3-dicarbonyl compound (722 mg, 5.55 mmol), GdCl3*6H2O (25 mg, 0.09 mmol) was added and the mixture was stirred at 80°C for 3.0 hr. After completion of the reaction (TLC), the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the corresponding 2-methyl benzimidazole. The crude material was further purified by through column chromatography by using 10percent ethyl acetate in hexane.General procedure: A mixture of 1a (0.54 g, 5 mmol), imidazolium chloride (0.09 g, 0.5 mmol) and N, N-dimethylbenzamide (0.55 g, 7.5 mmol) in 5mL xylene was heated to 140 °C and stirred at this temperature for 8 h. When the reaction was completed, 50mL water was added and the resulting mixture was extracted with 50 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 using petroleum ether and ethyl acetate as the eluent or recrystallized from petroleum ether/EA to give the desired products.

5,6-Dichloro-2-methylbenzimidazole is a benzimidazole with antiparasitic activity. It also shows aminopyrine demethylase-inhibiting activity.

Molecular Weight:201.05
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:199.9908036
Monoisotopic Mass:199.9908036
Topological Polar Surface Area:28.7
Heavy Atom Count:12
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes