反应详情

温度

80 °C

To a solution of ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate (1.19 g, 4.68 mmol) in anhydrous dioxane (50.0 mL) was added potassium carbonate (1.29 g, 9.36 mmol) and bromomethyl-2,2-difluorocyclopropane (1.00 g, 5.85 mmol). The reaction mixture was heated at 80° C. for 16 h, filtered and the solid was washed with ethyl acetate (100 mL). The filtrate was concentrated in vacuo and the residue was recrystallized from ethyl acetate in hexane to afford the title compound as a yellow solid (0.87 g, 54%): mp 146-148° C.; 1H NMR (300 MHz, CDCl3) δ 4.18 (q, J=7.1 Hz, 2H), 3.99 (t, J=8.4 Hz, 2H), 3.65-3.44 (m, 3H), 3.20-3.12 (m, 1H), 2.48 (s, 3H), 2.02-1.88 (m, 1H), 1.68-1.55 (m, 1H), 1.38-1.28 (m, 1H), 1.23 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.5, 160.1, 156.8, 155.2, 114.9 (t), 113.8, 60.8, 42.4, 42.1, 41.1 (d), 20.3 (t, 2JC-F=43 Hz), 17.5, 14.9 (t, 2JC-F=43 Hz), 14.6; MS (ES+) m/z 399.0 (M+1).

1. filtrationfiltered
2. washthe solid was washed with ethyl acetate (100 mL)
3. concentrationThe filtrate was concentrated in vacuo
4. customthe residue was recrystallized from ethyl acetate in hexane