Phosgene → Benzimidazol-2-one

HRID 359899Notes

Reaction equation

HRID 359899 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]1([NH2:12])[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].[OH-].[Na+]>O>[N:11]1[C:1](=[O:2])[N:12]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 7243O-PhenylenediamineHCID 14798Sodium Hydroxide

Product 1

HCID 162542Benzimidazol-2-oneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 g (1.01 mol) of phosgene are passed into 108 g (1 mol) of o-phenylenediamine in 800 ml of water at 80° C. over a period of 4 hours and the pH is kept constant at 6.5 by simultaneous metering in of 231 g (1.9 mol) of 50% strength aqueous sodium hydroxide solution. After filtration with suction and washing with water, 126 g of benzimidazol-2-one are obtained, which corresponds to a yield of 94% of theory.

Workup

  1. filtrationAfter filtration with suction
  2. washwashing with water, 126 g of benzimidazol-2-one
  3. customare obtained

Sources & evidence

ORD record
ord-596885558e0149dab94c58fc34b015c4
Source dataset
uspto-grants-1991_03
Patent number
US05003079

Reaction notes

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