Methanol → HCID 178473121, compound

Participants

Reaction Steps

A solution of 5-methoxy-2-benzimidazolethiol (200 mg, 1.11 mmol) and ethyl 3-bromopyruvate (0.20 mL, 1.43 mmol) in methanol (5 mL) and acetone (2 mL) was shaken at room temperature for 4 hours. The solvents were removed under the reduced pressure on a rotary evaporator. The residue was triturated with ethyl acetate. Solvent was decanted and the residue was dissolved in methylene chloride. The solution was washed with diluted aqueous sodium bicarbonate solution and water, and then dried over magnesium sulfate. Removal of the solvent gave the expected product, 3-(5-Methyl-1H-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (300 mg, 92%). 1H-NMR (D3COD, 300 MHz) δ (ppm): 7.19 (br. s, 1H), 6.75 (br. s, 1H), 6.69 (dd, J=2.3 Hz, J=8.8 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 4.29 (br. s, 1H), 3.93 (br. s, 1H), 3.69 (s, 3H), 1.24 (t, J=7.1 Hz, 3H). MS (ESI): m/z 295 (M+1, 100).

Provenance & Evidence