2,6-Dichlorobenzaldehyde → HCID 28370697, compound

To a solution of 4-nitro-benzene-1,2-diamine (1.5 g) and 2,6-dichloro-benzaldehyde (1.7 g) in DMSO (20 mL) was added a catalytic amount of FeCl3 and the mixture was stirred in an open flask at ambient temperature overnight. Resulting solution was diluted by aqueous NH4Cl and extracted twice with ethyl acetate. Combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was taken up in THF (10 mL) and mixed with conc NH4OH (5 mL). To the solution was added Na2S2O4 (2 g) as a solid and the mixture was stirred at ambient temperature for 24 h. After usual aqueous workup, the crude product obtained was purified by column chromatography on silica gel to give aerobically unstable 2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-ylamine: 1H NMR (CDCl3, 400 MHz) 7.4 (app d, 2H), 7.3 (m, 1H), 7.2 (m, 2H), 7.1 (app d, 1H), 6.7 (br, 1H), 3.7 (br, 2H).

1. extractionextracted twice with ethyl acetate
2. dry with materialCombined organics were dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. additionmixed with conc NH4OH (5 mL)
6. additionTo the solution was added Na2S2O4 (2 g) as a solid
7. stirringthe mixture was stirred at ambient temperature for 24 h
8. customAfter usual aqueous workup, the crude product obtained
9. customwas purified by column chromatography on silica gel

ORD record

ord-49fa96e9fd7040258130252e7470533f

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2