Ethanol → HCID 67041059, compound

Participants

Reaction Steps

Thionyl chloride (1 mL, 14.6 mmol) was added dropwise to 2-amino-2-(thiophen-2-yl)propanoic acid (0.500 g, 2.92 mmol) suspended in anhydrous ethanol (10 mL) at 0° then the reaction was heated at reflux for 22 hours. The reaction was concentrated by rotary evaporation, diluted with water (5 mL), adjusted pH to 9 with 6N aqueous sodium hydroxide, and extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as an oil (0.498 g, 2.499 mmol, 86%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.17 (t, J=7.17 Hz, 3 H) 1.60 (s, 3 H) 2.53 (s, 2 H) 4.11 (q, J=7.23 Hz, 2 H) 6.91-6.98 (m, 1 H) 7.00 (dd, J=3.68, 1.10 Hz, 1 H) 7.37 (dd, J=5.15, 1.10 Hz, 1 H). MS (DCI) m/z 200 (M+H)+, 217 (M+NH4)−.

Provenance & Evidence