Hydrochloric Acid → 2H-Benzimidazol-2-one,4-chloro-1,3-dihydro-(9CI)

Temperature

23 °C

To a solution of 3-chloro-benzene-1,2-diamine (0.820 g, 5.75 mmol) and THF (25 mL), was added carbonyl diimidazole (1.12 g, 6.90 mmol) at 0° C. The mixture was stirred for 16 h and allowed to warm to 23° C. A solution of 1M aqueous HCl (25 mL) was added to the reaction mixture at 0° C., followed by water (100 mL) and the mixture was stirred for 1 h. The precipitated solid was filtered and dried under high vacuum for 18 h to yield the titled compound, which was used in the next step without further purification (0.800 g, 83%). MS (ESI/CI): mass calcd. for C7H6ClN2O, 168.0; m/z found, 169.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 11.13 (s, 1H), 10.88 (s, 1H), 7.00-6.86 (m, 3H).

1. stirringthe mixture was stirred for 1 h
2. filtrationThe precipitated solid was filtered
3. customdried under high vacuum for 18 h

ORD record

ord-a312fd480d104a42b471afd7fa5cd6ca

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759345B2