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

Temperature

100 °C

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.)

1. temperatureCooling to RT
2. customby partition between water (100 ml) and ethyl acetate (EtOAc, 100 ml)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with EtOAc (3×; 30 ml)
5. washThe combined organic phases were washed with saturated NaCl solution (80 ml)
6. dry with materialdried over MgSO4
7. customThe solvent was removed under reduced pressure in a rotary evaporator
8. customTrituration of the residue with EtOAc (10 ml) triturated

ORD record

ord-144f2039344c4a5a85fed12f8250de0e

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652143B2