Sodium hydride → HCID 66692195, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(methyl-thio)-2-nitro-N-(pyridin-3-ylmethyl) aniline (0.8 g, 0.002 mol) in THF (20 ml) was added NaH (60% suspension in mineral oil), (0.14 g, 0.006 mol) and the resulting solution was continued to stir at 60° C. for 8 h. The reaction was quenched with ice chips and extracted with dichloromethane (3×100 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford to afford the crude compound which was purified by chromatography to obtain title compound 5-(methyl-thio)-2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-ol as an off white solid. 1H NMR (400 MHz, DMSO-d6), δ: 12.28 (bs, 1H), 9.36 (s, 1H), 8.71-8.70 (m, 1H), 8.55-8.53 (d, J=8 1H), 7.62-7.59 (m, 2H), 7.52-7.50 (d, J=8 Hz, 1H), 7.28-7.26 (dd, J=1.2 Hz, J=8 Hz, 1H), 2.53 (s, 3H). MS (M+1): 258.

Provenance & Evidence