Iodoethane → HCID 69640512, compound

tert-Butyl (4-bromo-1H-imidazol-1-yl)carbamate (1.16 g, 4.43 mmol) was dissolved in N,N-dimethylformamide (DMF, 12 mL) and treated with sodium hydride (0.310 g, 7.75 mmol, 60% dispersion in oil). After 45 minutes, the mixture was cooled on an ice bath and was treated with iodoethane (0.828 g, 5.31 mmol). The ice bath was removed after five minutes of stirring and the reaction was stirred for an additional 90 minutes. The reaction mixture was diluted with aqueous potassium carbonate (50 mL, 5% w/w) and the product was extracted with ethyl acetate. The organics were washed with 5% aqueous potassium carbonate and brine and dried over sodium sulfate. The organic layer was concentrated and the residue was purified using silica gel chromatography (0-10% methanol/dichloromethane) to afford the title compound (1.023 g, 3.53 mmol, 80%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J=1.5 Hz, 1H), 6.93 (d, J=1.5 Hz, 1H), 3.71 (q, J=7.2 Hz, 2H), 1.44 (s, 9H), 1.16 (t, J=7.2 Hz, 3H); ESIMS m/z 290 ([M+H]+).

1. temperaturethe mixture was cooled on an ice bath
2. customThe ice bath was removed after five minutes
3. stirringthe reaction was stirred for an additional 90 minutes
4. additionThe reaction mixture was diluted with aqueous potassium carbonate (50 mL, 5% w/w)
5. extractionthe product was extracted with ethyl acetate
6. washThe organics were washed with 5% aqueous potassium carbonate and brine
7. dry with materialdried over sodium sulfate
8. concentrationThe organic layer was concentrated
9. customthe residue was purified

ORD record

ord-3c5c30ae6d6d4ab79cc8123f271fd5b0

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680121B2