Water → HCID 178508184, compound

HRID 1367862Notes

Reaction equation

HRID 1367862 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-c8eaa3241607427aa0ca7dd253098157
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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