Cyanogen Bromide → 2-Aminobenzimidazole

HRID 1988582Notes

Reaction equation

HRID 1988582 reaction equation
[N:1]#[C:2]Br.[NH2:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:6]=1OC.[OH-].[Na+]>CCO.O>[NH2:1][C:2]1[NH:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[N:11]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 1842683-Methoxybenzene-1,2-diamine

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Cyanogen bromide (7.05 mmol, 0.74 g) was added to a solution of 2,3-diaminoanisole (4.7 mmol, 0.65 g) in EtOH (10 mL) and the reaction was stirred at room temperature for 14 h. The reaction was diluted with H2O and then basified (pH>12) using 4 M NaOH. The aqueous layer was extracted with CH2Cl2. The organic phase was then separated and washed with brine and then dried over MgSO4 and then concentrated to provide 2-aminobenzimidazole 37b.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. customThe organic phase was then separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-53f3d065292e4467af65766f65fb3d62
Source dataset
uspto-grants-2010_01
Patent number
US07642265B2

Reaction notes

Loading…