Phosphorus oxychloride → HCID 45078587, compound

Temperature

80 °C

Phosphorus oxychloride (10 mL) was added to 4-chloro-1,3-dihydro-benzoimidazol-2-one (0.750 g, 4.45 mmol), and the mixture heated to 80° C. for 48 h. The mixture was cooled to 23° C. and POCl3 removed under reduced pressure. The residue was cooled to 0° C., and cold saturated aqueous NaHCO3 (20 mL) was added cautiously. After stirring at 23° C. for 15 min, the mixture was sonicated and the resulting residue was filtered to yield the titled compound (0.760 g, 92%), which was used in the next step without further purification. MS (ESI/CI): mass calcd. for C7H5Cl2N2, 186.0; m/z found, 187.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 13.68 (s, 1H), 7.51-7.42 (m, 1H), 7.32-7.25 (m, 1H), 7.22 (m, 1H).

1. temperatureThe mixture was cooled to 23° C.
2. customPOCl3 removed under reduced pressure
3. temperatureThe residue was cooled to 0° C.
4. additioncold saturated aqueous NaHCO3 (20 mL) was added cautiously
5. customthe mixture was sonicated
6. filtrationthe resulting residue was filtered

ORD record

ord-c13fa8e1022e419ca40288e905e7eda0

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865713B2