Ammonia → 3-Methyl-4-bromo-5-aminobenzimidazole

HRID 2299125Notes

Reaction equation

HRID 2299125 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[Br:12]Br.N>CC(O)=O>[CH3:1][N:2]1[C:6]2[C:7]([Br:12])=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 136802831-Methyl-1H-benzimidazol-6-amine

Product 1

HCID 129684523-Methyl-4-bromo-5-aminobenzimidazoleYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-methyl-5-aminobenzimidazole (0.27 g, 1.8 mmol) in 10 ml of AcOH was added Br2 (0.10 ml). The reaction mixture was stirred for 1 h at 25° C. and concentrated in vacuo, yielding an oil which was subjected to column chromatography (NH3 sat'd 3% MeOH/CHCl3) to yield 0.14 g (0.62 mmol, 35%) of the desired product.

Workup

  1. concentrationconcentrated in vacuo
  2. customyielding an oil which

Sources & evidence

ORD record
ord-5fd852d0bb6643d6911bf374c2769674
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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