Dimethylformamide → HCID 59497300, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-acrylic acid ethyl ester (0.1 g, 0.27 mmol) in DMF (1 mL) was added NaOCH3 (1.1 mL, 0.5 M in MeOH). The reaction mixture was stirred at 60° C. for 2 h (due to poor solubility, the reaction was heated). The reaction mixture was concentrated. The reaction mixture was diluted with 1N HCl and then extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated. Since LCMS indicated that there was a small amount of the product in methyl ester form, the resulting residue was diluted with methanol and treated with 2N NaOH for 30 min. The mixture was acidified by adding 1N HCl and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 39 mg of the title compound as an off-white solid. LCMS (ESMS): m/z 377.31 (M+H+).

Provenance & Evidence