Water → HCID 178508184, compound

HRID 1910133Notes

Reaction equation

HRID 1910133 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11])([O-:3])=[O:2].Br[C:13]#[N:14].O>C(O)C>[N+:1]([C:4]1[C:5]2[NH:11][C:13]([NH2:14])=[N:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 178508184HCID 178508184, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.53 g (10 mmol) of 3-nitro-benzene-1,2-diamine in ethanol (20 mL) was added 1.3 g (12.5 mmol) of BrCN and water (5 mL). The mixture was refluxed for 1.0 h. After cooling to room temperature, the solvent was concentrated, then the residue was dissolved in water, the pH was adjusted to 8.0 with sat. NaHCO3 solution. The resulting solid was filtered, washed with water and dried under vacuum to afford 1.42 g (80%) of the 7-nitro-1H-benzoimidazol-2-ylamine. LCMS: 179 (M+1)+.

Workup

  1. temperatureThe mixture was refluxed for 1.0 h
  2. concentrationthe solvent was concentrated
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-50423a9292434b66a3664f40d2a47687
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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