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

HRID 730381Notes

Reaction equation

HRID 730381 reaction equation
OS([O-])=O.[Na+].[CH:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=O.[C:18]1([NH2:25])[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>C(O)C>[NH:24]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:25]=[C:6]1[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=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 100.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of NaHSO3 (20.0 mL, 40% in water) was treated with a solution of methyl 4-formylbenzoate (2.20 g, 13.4 mmol) in ethanol (15.0 mL) and stirred at ambient temperature for 1 h. 1,2-benzenediamine (1.45 g, 13.4 mmol) was added and the solution was heated to reflux overnight. Upon cooling, the solution was poured into ice water and the resultant precipitate was collected by filtration, washed with water, and dried in vacuo to provide the title compound as a grey solid (3.40 g; 100%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.19 (d, J=7.8 Hz, 2 H) 8.15 (d, J=7.8 Hz, 2 H) 7.70 (s, 2 H) 7.34 (dd, J=6.1, 3.3 Hz, 2 H) 3.98 (s, 3 H). MS(ES+) m/e 253 [M+H]+.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. temperatureUpon cooling
  4. filtrationthe resultant precipitate was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2db42d6174f9474c914deeeeeff0ba03
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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