Benzaldehyde → 6-Bromo-2-phenyl-1H-benzimidazole

HRID 2203239Notes

Reaction equation

HRID 2203239 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 129487756-Bromo-2-phenyl-1H-benzimidazoleYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromobenzene-1,2-diamine (0.5 g, 2.67 mmol), benzaldehyde (0.284 g, 2.67 mmol), and 4-methylbenzenesulfonic acid (0.046 g, 0.267 mmol) in DMF (8 mL) were combined and heated at 100° C. for 1 hour in a microwave reactor. The reaction mixture was subsequently diluted with EtOAc, washed with brine (4×100 mL), concentrated, and purified by CombiFlash® chromatography, eluting with a gradient of MeOH (0-30%) in DCM over 120 minutes. The product-containing fractions were combined and concentrated to give the title compound as light yellow liquid (0.48 g, 66%).

Workup

  1. washwashed with brine (4×100 mL)
  2. concentrationconcentrated
  3. custompurified by CombiFlash® chromatography
  4. washeluting with a gradient of MeOH (0-30%) in DCM over 120 minutes
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0bab69c83c4bd580e00d3499ebb052
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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