Cyanogen Bromide → HCID 178508200, compound

HRID 1845110Notes

Reaction equation

HRID 1845110 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-ab04dacf0fd54cb39df8a5c16eb4c03b
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

Loading…