Methyl iodide → 1,4,4,5,5-Pentamethylimidazolidin-2-one

To a solution of 4,4,5,5-tetramethylimidazolidin-2-one (100 mg; 0.70 mmol) in dry tetrahydrofuran (5 ml), a 1.57 N solution of n-butyl lithium in hexane (0.49 ml; 0.77 mmol) was added at 0° C. After stirring at the same temperature for 5 minutes, a solution of methyl iodide (109 mg; 0.77 mmol) in tetrahydrofuran (1 ml) was added at 0° C., followed by stirring at room temperature for 10 minutes. To the reaction mixture, a saturated aqueous solution of potassium dihydrogen phosphate was added to decompose the excess reaction agent, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give an oily residue, which was purified by thin layer chromatography (chloroform:acetone=1:1) to give 1,4,4,5,5-pentamethylimidazolidin-2-one as a colorless solid.

1. stirringby stirring at room temperature for 10 minutes
2. extractionthe resulting mixture was extracted with ethyl acetate
3. washThe extract was washed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customto give an oily residue, which
7. customwas purified by thin layer chromatography (chloroform:acetone=1:1)

ORD record

ord-20766a39d8a142b096adeb33c814deab

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05231179