Hydrochloric Acid → HCID 178477825, compound

Temperature

130 °C

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)+.

1. customwas split evenly between four 20 mL reaction vials
2. customthe vials were sealed
3. temperatureAfter cooling to rt
4. filtrationthe resulting solids were collected by filtration
5. washwashed with ethanol
6. dissolutionThen the isolated solid was dissolved in 250 mL of water
7. temperatureby heating to 80° C
8. additionTo this solution was added slowly 25 mL of saturated aqueous NaHCO3
9. temperaturecooled in an ice-bath
10. filtrationThe resulting white solid was collected by filtration
11. dissolutiondissolved in 3:1 CH2Cl2/methanol
12. dry with materialdried (MgSO4)
13. customevaporated
14. customThe resulting solid was sonicated with CH2Cl2
15. customevaporated (2×)

ORD record

ord-d1021d4da28940e2914fe805ab9cc56a

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410284B2