Water → 2-p-Tolyl-1H-benzoimidazole

HRID 1111091Notes

Reaction equation

HRID 1111091 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[C:10]1([NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].O.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1(C)C=CC=CC=1>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:17]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 77254-MethylbenzaldehydeHCID 178418268HCID 178418268, compound

Product 1

HCID 7259822-p-Tolyl-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 120.2 g (1 mole) of 4-tolualdehyde and 108.1 g (1 mole) of o-phenylenediamine in toluene is heated at reflux with azeotropic removal of water. After 20 hours at reflux, the reaction is cooled to room temperature, then 443.4 g (1 mole) of lead tetraacetate is added, and the reaction is stirred at room temperature for 20 hours The solids are removed by filtration, and the filtrate is swirled with basic alumina. The mixture is filtered, and the filtrate is evaporated to dryness The product is purified by recrystallization from ethanol.

Workup

  1. temperatureAfter 20 hours at reflux
  2. customare removed by filtration
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated to dryness The product
  5. customis purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-688dd972cfc64ce69e1a9467b0760599
Source dataset
uspto-grants-1990_12
Patent number
US04978476

Reaction notes

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