Hydrochloric Acid → HCID 178477825, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-4-iodo-1,2-phenylenediamine 1-6 (8.00 g, 29.8 mmol), 2.48 mL of 12 M HCl (29.8 mmol), triethyl orthoformate (39.7 mL, 238.4 mmol) in 30 mL ethanol was split evenly between four 20 mL reaction vials; the vials were sealed and stirred at 130° C. for 10 min each. After cooling to rt, the resulting solids were collected by filtration and washed with ethanol. Then the isolated solid was dissolved in 250 mL of water by heating to 80° C. To this solution was added slowly 25 mL of saturated aqueous NaHCO3. The mixture was confirmed to have a pH >8, and then cooled in an ice-bath. The resulting white solid was collected by filtration and then dissolved in 3:1 CH2Cl2/methanol, dried (MgSO4) and evaporated. The resulting solid was sonicated with CH2Cl2 and evaporated (2×) to provide 6-chloro-5-iodobenzimidazole 1-7 as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 7.87 (br s, 1H), 8.17 (br s, 1H), 8.28 (s, 1H), 12.66 (br s, 1H); LC-MS: calculated for C7H4ClIN2 277.9, observed m/e 279.1 (M+H)+.

Provenance & Evidence