Potassium Carbonate → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-one

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one (4.50 g, 20.00 mmol), tetrabutylammonium iodide (0.10 g) and potassium carbonate (4.00 g, 28.92 mmol) in 1,4-dioxane (100 mL) was added 2-cyclopropylethyl-4-methylbenzenesulfonate (6.00 g, 24.96 mmol). The reaction mixture was heated to reflux for 37 h. The solvent was removed in vacuo. The residue was dissolved in water (50 mL) and extracted with ethyl acetate. The organic solution washed with water and brine and dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography to afford 1-(5-acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-one in 37% yield (2.20 g): mp 82-83° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 4.12-4.06 (m, 2H), 3.63-3.57 (m, 2H), 3.40 (t, J=7.2 Hz, 2H), 2.60 (s, 3H), 2.44 (s, 3H), 1.51-1.44 (m, 2H), 0.71-0.62 (m, 1H), 0.49-0.43 (m, 2H), 0.09-0.04 (m, 2H); MS (ES+) m/z 294.2 (M+1).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 37 h
3. customThe solvent was removed in vacuo
4. dissolutionThe residue was dissolved in water (50 mL)
5. extractionextracted with ethyl acetate
6. washThe organic solution washed with water and brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated in vacuo
10. customthe residue was purified by column chromatography

ORD record

ord-3eb151d0371241bdb6bdb320d0c1d826

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08049016B2