Potassium Iodide → HCID 9861236, compound

Temperature

80 °C

A mixture of 5-bromo-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (2.5 g, 8 mmol), benzyl bromide (1.2 mL, 10 mmol), potassium carbonate (1.38 g, 10 mmol), and potassium iodide (50 mg) in anhydrous acetonitrile was heated at 80° C. under nitrogen for 1 hour. The reaction mixture was cooled to room temperature and treated with a saturated aqueous ammonium chloride solution (30 mL) and ethyl acetate (50 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (30 mL) and dried (MgSO4). After removal of the solvent, the residue was taken up in trifluoroacetic acid (10 mL, neat) and the solution was stirred at room temperature under nitrogen for 10 minutes. The reaction solution was then treated with brine (30 mL) and ethyl acetate (50 mL). The organic layer was separated and dried (MgSO4). After removal of the solvent, the residue was applied to a pad of silica gel to afford the title compound as white solid (1.89, 78%): mp 245-246 ° C; 1H-NMR (DMSO-d6) δ11.2. (s, 1H), 7.37-7.27 (m, 6H), 7.13 (dd, 1H, J=8.25, 2.25 Hz), 6.95 (d, 1H, J=8.25 Hz), 5.0 (s, 2H); MS (ES) m/z 301((M−H)−, 50%), 303((M−H)−, 50%).

1. temperatureThe reaction mixture was cooled to room temperature
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with ethyl acetate (3×30 mL)
4. washThe combined organic layers were washed with brine (30 mL)
5. dry with materialdried (MgSO4)
6. customAfter removal of the solvent
7. additionThe reaction solution was then treated with brine (30 mL) and ethyl acetate (50 mL)
8. customThe organic layer was separated
9. dry with materialdried (MgSO4)
10. customAfter removal of the solvent

ORD record

ord-5f6669417db94e53bb9081193f939917

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380235B1