Dimethylformamide → 4,5,6-trichloro-1H-benzoimidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,3,4-trichloro-6-nitro-phenylamine (0.250 g, 1.04 mmol), sodium dithionite (0.907 g, 5.21 mmol), trimethyl orthoformate (4 ml), DMF (4 mL), and acetic acid (0.5 mL) was heated in a sealed tube for 15 h at 100° C. The reaction mixture was cooled to 23° C. and partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was collected and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, and concentrated to yield the titled compound (0.098 g, 43%). MS (ESI/CI): mass calcd. for C7H3Cl3N2, 219.9; m/z found, 221.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.16 (s, 1H), 8.43 (s, 1H), 7.90 (s, 1H).

Provenance & Evidence