Water → HCID 58790361, compound

Temperature

0 °C

To a stirred solution of 4-iodo-1H-imidazole (291, 2 g, 10.3 mmol) La) Y. He et al., Tet. Lett. 45, 2004, 5529-5532, b) Panosyan, F. B., Still, I. W. J., Can. J. Chem. 79, 2001, 1110-1114.] in dry tetrahydrofuran (40 mL) at 0° C. under nitrogen was added sodium hydride (60% in oil, 0.91 g, 22.7 mmol). The mixture was stirred for 20 min. at 0° C., 1-bromo-3-chloropropane (1.2 mL, 12.4 mmol) was added and stirring was continued for 24 h at room temperature. Water was added and the aqueous solution was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent ethyl acetate-dichloromethane, 4:96) to afford 292 (1.35 g, 5.0 mmol, 49% yield) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.63 (d, J=1.2 Hz, 1H), 7.42 (d, J=1.2 Hz, 1H), 4.08 (t, J=6.8 Hz, 2H), 3.55 (d, J=6.8 Hz, 2H), 2.16 (q, J=6.8 Hz, 2H). MS (m/z): 271.0 (M+H, 100%), 273.0 (M+H, 32%).

1. stirringstirring
2. waitwas continued for 24 h at room temperature
3. extractionthe aqueous solution was extracted twice with ethyl acetate
4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
5. customthe solvent was removed under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (eluent ethyl acetate-dichloromethane, 4:96)

ORD record

ord-91c1babae17744669ddddf2f4e851a56

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329726B2