Ethyl 2-cyanopropionate → Ethyl 2-carbamothioyl-2-methylacetate

Participants

Reaction Steps

A mixture of diphenylphosphinodithioic acid (Alfa-Aesar) (7.48 g, 29.9 mmol) and 2-cyanopropionic acid ethyl ester (ABCR, 1.980 mL, 14.94 mmol) in isopropanol (80 mL) was heated under reflux for 8 h then stood at rt overnight. Reaction mixture was filtered and filtrate was diluted with EtOAc and washed with 1N NaOH, brine, and dried over Na2SO4. Crude was purified by chromatography on silica gel using a Hex/EtOAc gradient. Appropriate fractions were combined and evaporated to yield title compound as a yellow oily solid. 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.60 (s, 1H), 9.40 (s, 1H), 4.05 (q, 2H), 3.74 (q, 1H), 1.29 (d, 3H), 1.15 (t, 3H). [ES+MS] m/z 162 (MH+).

Provenance & Evidence