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

Participants

Reaction Steps

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one (2.25 g, 10.00 mmol), tetrabutylammonium iodide (0.10 g) and potassium carbonate (3.50 g, 25.27 mmol) in tetrahydrofuran (100 mL) was added cyclopropylmethyl bromide (2.0 mL, 20.88 mmol). The reaction mixture was heated to reflux for 50 hours. The solvent was removed in vacuo, and the residue was washed with water and hexanes to afford the title compound in 33% yield (0.94 g): mp 103-104° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 4.14-4.05 (m, 2H), 3.72-3.69 (m, 2H), 3.19 (d, J=6.0 Hz, 2H), 2.57 (s, 3H), 2.44 (s, 3H), 0.99-0.89 (m, 1H), 0.59-0.55 (m, 2H), 0.27-0.22 (m, 2H); MS (ES+) m/z 280.2 (M+1).

Provenance & Evidence