Cyanogen Bromide → 2-Aminobenzimidazole
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- extractionThe aqueous layer was extracted with CH2Cl2
- customThe organic phase was then separated
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4dd7d82b92d54646aeddc463d3d6f37d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207173B2
Reaction notes
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