Propyl mercaptan → HCID 22132962, compound

Participants

Reaction Steps

To a suspension of 6,6-dimethyl-3-methanesulphonyl-1-(pyrrolidin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (500 mg, 1.4 mmol) in EtOH (15 mL) was added NaOH (0.71 mL of a 4 M solution, 2.8 mmol) followed by propanethiol (255 μL, 2.8 mmol). The mixture was stirred at room temperature for 2 h then evaporated. The residue was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was triturated with ether and the colourless solid (380 mg, 77%) collected by filtration. mp 117-119° C. C18H25NO2S2 requires: C, 61.50; H, 7.17; N, 3.98%. Found: C, 61.48; H, 7.02; N, 3.97%. 1H NMR (250 MHz, CDCl3) δ1.04 (6H, s), 1.10 (3H, t, J=7.3 Hz), 1.87 (2H, sextet, J=7.3 Hz), 1.93-1.99 (4H, m), 2.40 (2H, s), 2.83 (2H, s), 3.00 (2H, t, J=7.3 Hz), 3.57-3.63 (4H, m). MS (ES+) 352 (M+1).

Provenance & Evidence