Difluoroacetic acid → HCID 66698044, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,3-diamino-5-nitroanisole (Horner et al., Annalen 1953, 579, 212) (1.10 g, 6 mmol) and difluoroacetic acid (2.31 g, 24 mmol) in polyphosphoric acid (PPA) (50 g) was heated at 130° C. in an oil bath for 1 hr. The hot solution was poured into water, and the pH was adjusted to neutral with cooling to give 2-(difluoromethyl)-4-methoxy-6-nitro-1H-benzimidazole (1.33 g, 91%): mp (EtOH/H2O) 192-194° C.; 1H NMR (DMSO-d6) δ 814.18 (br, exchangeable with D2O, 1H), 8.18 (br, 1H), 7.65 (dd, J=1.4 Hz, 1H), 7.30 (t, JHF=52.9 Hz, 1H), 4.07 (s, 3H); Anal. Calcd. for C9H7F2N3O3: C, 44.45; H, 2.9; N, 17.3. Found: C, 44.75; H, 3.0; N, 17.3%.

Provenance & Evidence