O-Phenylenediamine → 2-Hydroxy benzimidazole

HRID 478905Notes

Reaction equation

HRID 478905 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C1N=CN([C:14](N2C=NC=C2)=[O:15])C=1>CN(C)C=O>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:14]1=[O:15]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 119852-Hydroxy benzimidazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1,2-phenylenediamine (10.00 g, 0.092 mol) in dimethylformamide (150 cm3) was added 1,1′-carbonyldiimidiazole (CDI, 14.99 g, 0.092 mol). After 22 hours, the reaction mixture was evaporated and then slurried in ethyl acetate. The resulting mixture was filtered, washed with ethyl acetate, and the residue dried in vacuo to give 1,3-dihydrobenzoimidazol-2-one (12.10 g, 98%) as a white solid:

Workup

  1. customthe reaction mixture was evaporated
  2. filtrationThe resulting mixture was filtered
  3. washwashed with ethyl acetate
  4. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-1a529997a9434578a7b81fc9e13987b7
Source dataset
uspto-grants-2003_11
Patent number
US06642256B2

Reaction notes

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