3-Bromoaniline → 1-(3-Bromophenyl)imidazolidin-2-one

1-Chloro-2-isocyanatoethane (1.18 mL, 13.8 mmol) was added dropwise to a solution of 3-bromoaniline (1.5 mL, 13.8 mmol) in DMF (30 mL) at 0° C. then stirred at room temperature for 16 hr, then 70° C. for 2 hr. The solution was cooled to room temperature and 1-chloro-2-isocyanatoethane (0.40 mL, 4.69 mmol) was added. After stirring at room temperature for 2 hr, the solution was diluted with DMF (120 mL), cooled to 0° C. and NaH (660 mg, 60% dispersion in mineral oil, 16.5 mmol) added in portions. The mixture was stirred at room temperature for 64 hr, then diluted with EtOAc. After washing with H2O three times then brine the solution was dried over Na2SO4, concentrated in vacuo and the residue purified by silica gel chromatography (EtOAc/hexanes) to give 1-(3-bromophenyl)-2-imidazolidinone as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.56-3.62 (m, 2H), 3.88-3.92 (m, 2H), 5.20 (br s, 1H), 7.15-7.20 (m, 2H), 7.49-7.51 (m, 1H), 7.71 (s, 1H).

1. wait70° C. for 2 hr
2. temperatureThe solution was cooled to room temperature
3. stirringAfter stirring at room temperature for 2 hr
4. temperaturecooled to 0° C.
5. stirringThe mixture was stirred at room temperature for 64 hr
6. washAfter washing with H2O three times
7. dry with materialbrine the solution was dried over Na2SO4
8. concentrationconcentrated in vacuo
9. customthe residue purified by silica gel chromatography (EtOAc/hexanes)

ORD record

ord-fa1ed8a1f0ab4c3abc94518f0346cf14

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822518B2