Sodium Iodide → HCID 69139206, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-imidazolidinethione (1.02 g, 10 mmol), ethyl 3-bromopyruvate (1.95 g, 10 mmol), potassium carbonate (1.38 g, 10 mmol), sodium iodide (10 mg), Adogen (200 mg) in N,N-dimethyl formamide (15 mL) was stirred at 20° C. for 15 hours under nitrogen. The reaction mixture was diluted with water and then extracted ethyl acetate. Organic phase was dried over sodium sulfate, evaporated, and chromatographed (silica gel, dichloromethane-methanol 9:1), giving the expected product, 3-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester, as a brown solid (1.8 g, 83%). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 4.36 (d, J=7.1 Hz, 2H), 4.25-4.00 (m, 3H), 3.57 (d, J=11.2 Hz, 1H), 3.50-3.35 (m 1H), 3.25-3.10 (m, 1H), 1.37 (t, J=7.1 Hz, 3H).

Provenance & Evidence