Cyanogen Bromide → HCID 178508200, compound

HRID 1368001Notes

Reaction equation

HRID 1368001 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].Br[C:13]#[N:14]>C(O)C.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]2[NH:10][C:13]([NH2:14])=[N:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178508200HCID 178508200, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7.6 g (50 mmol) of 4-nitro-ortho-phenylenediamine was dissolved were dissolved in 100 mL of ethanol and 20 mL of H2O. 7.9 g (75 mmol) of BrCN was added in one portion to this stirring solution, and the resulting mixture was heated under reflux for 1.0 h. The reaction mixture was cooled to room temperature, concentrated to 20 mL then neutralized with saturated NaHCO3 solution to pH 8, and resulting solid 5-nitro-1H-benzoimidazol-2-ylamine collected via filtration was used directly in the next step without further purification.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1.0 h
  3. concentrationconcentrated to 20 mL

Sources & evidence

ORD record
ord-a54b3feb1e4b424bb907d2db8507796c
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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