Acetonitrile → HCID 136052376, compound

Participants

Reaction Steps

To a solution (40 mL) of methyl 2-amino-5-ethylthiophene-3-carboxylate (1 g) in methylene chloride were added triphosgene (0.69 g) and triethylamine (1.2 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 4-aminobenzonitrile (1.28 g), and the mixture was further stirred at room temperature for 1 hr, and the precipitated solid was collected by filtration. The obtained solid was dissolved in methanol (40 mL), sodium methoxide (0.73 g) was added, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was neutralized with hydrochloric acid (10% methanol solution), and the precipitated solid was collected by filtration. The obtained to solid was dissolved in acetonitrile (50 mL), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (2.3 g) and potassium carbonate (1.5 g) were added, and the mixture was stirred at 50° C. for 2 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography and dissolved in tetrahydrofuran (4 mL) and acetone (4 mL). 1N Aqueous sodium hydroxide solution (2 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH 7 with water and 1N hydrochloric acid, and extracted with chloroform. The obtained chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.18 g, 6%).

Provenance & Evidence