Ethanol → HCID 25205624, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-cyano-3-thiophen-2-yl-thioacrylamide (4.38 g, 22.5 mmol) and 1-boc-3-pyrrolidine synthesized from pyrrolidinol by reference procedures (Synthetic Commun. 1985, 15(7), 587-598) (4.16 g, 22.5 mmol) in 200 ml of anhydrous ethanol was added morpholine (3.94 g, 45 mmol) at room temperature with stirring. The resulting mixture was heated to reflux overnight. Then, 2-chloroacetamide (4.21 g, 45 mmol) and K2CO3 (6.23 g, 45 mmol) were added. The reaction mixture was continued to heat at 80° C. overnight and then cooled to room temperature. The crystals was filtered and washed with ethanol and water to give the desired product as yellow crystals. 1H-NMR (300 MHz, DMSO-d6): δ 7.92 (dd, J=1.2, 5.1 Hz, 1H), 7.33 (dd, J=1.2, 3.6 Hz, 1H), 7.30 (dd, J=3.6, 5.1 Hz, 1H), 7.26 (brs, 1H), 5.97 (d, J=10.5 Hz, 2H), 4.70 (d, J=6.0 Hz, 2H), 4.45 (d, J=10.5 Hz, 2H), 1.42 (m, 9H). ES MS m/z 417 (M+H)+, 415 (M−H)−.

Provenance & Evidence