Lawesson's reagent → HCID 178488795, compound

Participants

Reaction Steps

To a stirring solution of Lawesson's reagent (0.075 g, 0.185 mmol) in toluene (10 mL), was added starting material 158a (0.10 g, 0.33 mmol). Reaction mixture was heated to reflux temperature. After overnight reaction, solvent was evaporated under reduced pressure. Crude product was dissolved in small amount of CH2Cl2 to load onto preparative-TLC and eluted with CHCl3:Acetone:EtOH (10:1:0.2) to give pure yellow solid 160 (0.07 g, 68%). 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=7.4 Hz, 2H), 7.56 (s, 1H), 7.35 (t, J=7.5 Hz, 2H), 7.28 (m, 1H), 6.97 (d, J=6.6 Hz, 1H), 6.62 (d, J=7.8 Hz, 1H), 6.37 (m, 1H), 5.13 (t, J=5.6 Hz, 2H), 5.03 (t, J=5.6 Hz, 2H), 3.86 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 171.92, 158.94, 147.52, 132.68, 129.92, 128.69, 128.14, 125.43, 120.96, 111.72, 110.22, 56.72, 56.63, 46.38. HRMS (EI) calcd for C16H16N4OS [M]+ 312.104. found 312.1039.

Provenance & Evidence