O-Phenylenediamine → Methyl 4-(1H-benzo[d]imidazol-2-yl)benzoate

HRID 375539Notes

Reaction equation

HRID 375539 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[CH:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=O.S(=O)(O)[O-].[Na+]>CO>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 15294Methyl 4-FormylbenzoateHCID 23665763Sodium Bisulfite

Product 1

HCID 2328806Methyl 4-(1H-benzo[d]imidazol-2-yl)benzoateYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1,2-diaminobenzene (6.59 g), methyl 4-formylbenzoate (10.0 g) and sodium bisulfite (6.60 g) in methanol (500 mL) is stirred at reflux for 6 hours. The mixture is filtered and the solvent evaporated to leave a yellow solid. This solid is recrystallized from ethyl acetate/ethanol to give 2.92 g of the title compound as an oil-white solid.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationThe mixture is filtered
  3. customthe solvent evaporated
  4. customto leave a yellow solid
  5. customThis solid is recrystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-0333e4b13f7e4467885533976d1c5c5b
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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