Dimethylformamide → HCID 66692733, compound

Participants

Reaction Steps

To a stirred solution of N-(3-amino-4-(methyl amino) phenyl) methane sulfonamide (0.3 g, 0.0013 mol) in the mixture of DMF (10 ml) and water (2 ml) was added OXONE® (1.02 g, 0.0016 mol) and followed by nicotinaldehyde (0.16 g, 0.0015 mol) was added portion wise with constant stirring. The reaction mixture was allowed to stir at room temperature for 3 h. The reaction mixture was concentrated on a high vacuo pump and diluted with cold water (10 ml) and extracted with ethyl acetate (3×15 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated in vacuo and purified by column chromatography on silica gel to afford the desired product N-[1-methyl-2-(pyridin-3-yl)-1H-benzimidazol-5-yl]methanesulfonamide (363) as a brown solid. 1H NMR (400 MHz, DMSO-d6), δ: 9.53 (bs, 1H), 9.04 (s, 1H), 8.75-8.77 (d, J=4.0 Hz, 1H), 8.28-8.26 (d, J=8.0 Hz, 1H), 7.68-7.57 (m, 3H), 7.24-7.21 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 2.91 (s, 3H). LCMS (ES) m/e MS (M+1=244), Purity 95.64%.

Provenance & Evidence