p-Toluenesulfonic acid → HCID 19374693, compound

Participants

Reaction Conditions

Reaction Steps

The solid obtained in step A (2.4 g, 48 mmol) was dissolved in acetone (70 mL). p-Toluenesulfonic acid (0.20 g, 1 mmol) was added and the mixture was stirred at refluxing temperature (56° C.) for 2h. The solvent was evaporated, the residue obtained was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate (20 mL) and brine. The ethyl acetate layer was dried over MgSO4 and evaporated to a green solid which was flash chromatographed (silica, hexane-ethyl acetate gradient) to provide a white solid (1.62 g, 90%). mp:125°-127° C. Cl-MS m/e 189 (M+H)+. 1HNMR (DMSO-d6):δ:7.44 (1H, 1s, CH); 7.44 (1H, d, J=5.0 Hz); 8.05 (1H, d, J=5.0 Hz); 8.24 (1H, 1s, CH=N). 13C NMR (DMSO-d6): δ:2125.96, 132.00, 133.64, 136.96, 137.12.

Provenance & Evidence