Toluene → Benzimidazole

HRID 1814720Notes

Reaction equation

HRID 1814720 reaction equation
O=C1C2C=C(C=O)C=CC=2C(=O)C2C1=CC=CC=2.[C:19]1([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH2:32])C=CC=CC=1.C1(C)C=CC=CC=1>C(O)(=O)C>[N:32]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][CH:19]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 68297N-Phenyl-o-phenylenediamineHCID 3443109,10-Dioxo-9,10-dihydroanthracene-2-carbaldehyde

Product 1

HCID 5798BenzimidazoleYield 139.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9,10-Dioxo-9,10-dihydro-anthracene-2-carbaldehyde (1.63 g, 6.9 mmol) and N-phenyl-1,2-phenylenediamine (1.27 g, 6.90 mmol) were introduced into a mixture of 80 mL of toluene and 10 mL of acetic acid, and the mixture was refluxed for 12 hours. Solvent was removed and ethanol was poured therein to crystallize it, and then the precipitate was filtered to obtain a benzoimidazole compound ([2-(1-phenyl-1H-benzoimidazole-2-yl)-anthraquinone], 1.14 g, 41%).

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. customSolvent was removed
  3. additionethanol was poured
  4. customto crystallize it
  5. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-a51f5a14f7a441c0b0a86718be818a05
Source dataset
uspto-grants-2005_04
Patent number
US06878469B2

Reaction notes

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