Dimethyl Sulfate → 2-chloro-1-methyl-1H-1,3-benzodiazole

Participants

Reaction Steps

To a solution of 2-chloro-1H-benzo[d]imidazole (3.0019 g, 19.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in 2.5 M sodium hydroxide solution (19.67 ml, 49.2 mmol, J. T. Baker) at 0° C. was added dimethyl sulfate (3.01 ml, 31.5 mmol, Riedel de Haen AG) dropwise. The reaction was allowed to stir for 1½ h. White precipitate was noted to form. The white precipitate was filtered, washed with water, and dried to give the title compound. LCMS showed product peak at 1.47 min (m+1=167.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.80 (s, 3 H) 7.21-7.28 (m, 1 H) 7.28-7.35 (m, 1 H) 7.59 (d, J=3.72 Hz, 1 H) 7.61 (d, J=3.72 Hz, 1 H)

Provenance & Evidence