Cyanogen Bromide → 2-Aminobenzimidazole

HRID 221519

Reaction equation

HRID 221519 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-4dd7d82b92d54646aeddc463d3d6f37d
Source dataset
uspto-grants-2012_06
Patent number
US08207173B2

Linked notes

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