Benzoyl isothiocyanate → HCID 86731951, compound

Participants

Reaction Steps

To a solution of tert-butyl 2-amino-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.104 g, 0.386 mmol, 1 eq) in dry ethanol (1 mL) under argon was added benzoyl isothiocyanate (0.15 mL, 1.08 mmol, 2.8 eq). The mixture was heated at reflux for 16 hours. The solvent was evaporated in vacuo. Purification by reverse-phase chromatography (10-100% CH3CN: Water ramp over 20 min) afforded the desired product tert-butyl 2-(3-benzoylthioureido)-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate as a pale yellow oil (0.057 g, 0.132 mmol, 34% yield). 1H NMR (400 MHz, DMSO) δ 14.72 (s, 1H), 11.89 (s, 1H), 8.06-7.95 (m, 2H), 7.69 (t, J=7.4, 1H), 7.57 (t, J=7.7, 2H), 4.78 (d, J=14.8, 1H), 4.66 (d, J=15.0, 1H), 3.80-3.63 (m, 1H), 2.93 (d, J=16.7, 1H), 2.50-2.44 (m, 1H), 1.59 (s, 9H), 1.30 (d, J=6.1, 3H).

Provenance & Evidence