Hydrochloric Acid → 4-bromo-1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-1H-benzo[d]imidazol-6-amine

Participants

Reaction Steps

To a solution of 4-bromo-1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-6-nitro-1H-benzo[d]imidazole (2.83 g, 6.86 mmol) in Methanol (40 mL) in a 250 ml round bottomed flask was added Tin(II)chloride dihydrate (9.29 g, 41.1 mmol) and HCl (1.875 mL, 61.7 mmol). The reaction mixture was left to stir at 50° for 3 h. The solvent was removed and diluted with water (100 mL) and this solution was decanted into a 250 mL Erlenmeyer flask. The brown residue remaining in the round bottomed flask was dissolved in 100 mL of EtOAc, washed with 1N NaOH, brine, dried and evaporated to yield a brown solid which was the expected compound 4-bromo-1-(3-chloro-2-methylbenzyl)-2-(fluoromethyl)-1H-benzo[d]imidazol-6-amine (2.49 g, 6.51 mmol, 95% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.45-2.48 (m, 3H) 5.33 (s, 2H) 5.47 (s, 1H) 5.58-5.62 (m, 1H) 6.28-6.33 (m, 2H) 6.93 (d, J=1.77 Hz, 1H) 6.98 (s, 1H) 7.28 (s, 1H) 7.32 (d, 2H). LC/MS: MS (ES+) m/e 383 [M+H]+.

Provenance & Evidence