1-Propanol → HCID 53648704, compound

Participants

Reaction Steps

A solution of 2-(3,3-Dimethyl-ureido)-4-oxo-4,5-dihydro-thiophene-3-carboxylic acid methyl ester (50 mg, 0.205 mmol) in n-propanol (5 mL) was treated with H2SO4 (5 microliters) and stirred at ambient temperature for 12 hours. Little reaction was observed so the temperature was increased to 100° C. Little reaction was observed after 2 hours so four angstrom seives were added and the reaction continued at 100° C. for two additional hours at which point sufficient product was observed. The mixture was then concentrated and the residue purified via radial chromatography on a 4 mm plate using hexanes/ethyl acetate (1/1) to afford the title compound as a white solid (31 mg, 0.108 mmol, 53%) 1H NMR (CDCL3, 400 MHz) 1.03 (t, 3H, J=7.3 Hz), 1.78-1.84 (m, 2H), 3.06 (s, 6H), 3.84-3.89 (m, 5H), 5.51 (s, 1H), 11.08 (s, 1H).

Provenance & Evidence