Formic Acid → 6-Bromo-4-methyl-1H-benzoimidazole
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[CH:11](O)=O>O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[N:9]=[CH:11][NH:8][C:6]=2[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-bromo-3-methylbenzene-1,2-diamine (2.02 g, 10 mmol) was added water (10 mL) followed by formic acid (1.16 mL, 30 mmol). The mixture was stirred at 100° C. for 6 hours before cooling to room temperature. A solid precipitated from the solution and was allowed to sit at room temperature for 2 days. To this mixture was then added 1 N KOH (35 mL) and the solids were isolated by vacuum filtration. The solids were air dried and recrystallized from CHCl3 (70 mL) to provide 6-bromo-4-methyl-1H-benzimidazole (0.82 mg, 39%). Additional batches of product were obtained from the CHCl3 mother liquors (1.01 g, 48%).
Workup
- temperaturebefore cooling to room temperature
- customA solid precipitated from the solution
- waitto sit at room temperature for 2 days
- additionTo this mixture was then added 1 N KOH (35 mL)
- customthe solids were isolated by vacuum filtration
- customdried
- customrecrystallized from CHCl3 (70 mL)
Sources & evidence
- ORD record
- ord-9e05a01057e24368826b316e8a46621f
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318762B2
Reaction notes
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