Potassium Iodide → 1-{[4-(Benzyloxy)phenyl]methyl}imidazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Imidazolidin-2-one (2.0 g; 23.23 mmol) was dissolved in dimethyl sulfoxide (DMSO; 30 ml). Potassium carbonate (3.10 g; 23.23 mmol), potassium iodide (0.95 g; 5.80 mmol) and 4-benzyloxybenzyl chloride (5.4 g; 23.23 mmol) were added thereto. The mixture was heated at 100° C. for 3 hours (h). Cooling to RT was followed by partition between water (100 ml) and ethyl acetate (EtOAc, 100 ml). The phases were separated and the aqueous phase was extracted with EtOAc (3×; 30 ml). The combined organic phases were washed with saturated NaCl solution (80 ml) and dried over MgSO4. The solvent was removed under reduced pressure in a rotary evaporator. Trituration of the residue with EtOAc (10 ml) triturated resulted in 1-(4-benzyloxybenzyl)-imidazolidin-2-one (2.10 g; 7.43 mmol). MS: 283.15 (M+H); Rt: 1.38 min (method: gradient 0 min 90% H2O (0.05% TFA) 1.9 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 10% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Provenance & Evidence