Water → 4-Amino-1,3-dihydro-2H-benzimidazol-2-one

HRID 1528199Notes

Reaction equation

HRID 1528199 reaction equation
[C:1]1([NH2:9])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].[OH2:10].[C:11](#N)C>>[NH2:7][C:3]1[C:2]2[NH:8][C:11](=[O:10])[NH:9][C:1]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 690991,2,3-Triaminobenzene

Product 1

HCID 150200594-Amino-1,3-dihydro-2H-benzimidazol-2-oneYield 42%

Procedure

0.53 g (6.5 mmol, 2 eq) of N—N′-carbonyliimidazole were added portionwise to 450.7 mg (3.24 mmol, 1 eq) of benzene-1,2,3-triamine in solution in 30 ml of acetonitrile. The reaction medium was stirred at ambient temperature for 6 hours and then heated at 70° C. overnight. The reaction was stopped by adding 50 ml of water and then extracted with ethyl acetate. The organic phases were combined, and dried over sodium sulfate. The solvents were evaporated off and then the residue was purified by chromatography on silica gel (dichloromethane/methanol/aqueous ammonia: 95/5/2). 229.9 mg of 4-amino-1,3-dihydrobenzoimidazol-2-one were obtained. Yield=42%.

Workup

  1. temperatureheated at 70° C. overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were evaporated off
  5. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol/aqueous ammonia: 95/5/2)

Sources & evidence

ORD record
ord-161af9861d8f4d54b2657c2b6e23be57
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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