Hydrochloric Acid → 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-amine

Participants

Reaction Steps

To a 250 mL round-bottom flask containing MeOH (100 mL) was added crude 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (7.1 g, 15.56 mmol), tin(II) chloride dihydrate (10.53 g, 46.7 mmol) and hydrochloric acid (6.48 mL, 78 mmol). The resultant suspension was heated to 60° C. and monitored by LC/MS. By LC/MS the reaction was complete in 30 minutes. After the reaction had cooled to rt, the majority of the MeOH was removed in-vacuo and sodium carbonate (150 mL, 150 mmol) was added slowly to adjust the pH to about 10 and the mixture was extracted with Et2O (150 mL) and the organic was washed with H2O and brine and dried over MgSO4 and filtered. The solvent was removed in-vacuo leaving the desired product (4.7 g, 11.03 mmol, 70.9% yield) as crude brown solid that by LC/MS was sufficiently pure to use in the next step. MS (ES+) m/e: 425.1, 426.0 [M+H]+

Provenance & Evidence