Bromine → 2-Cyclopropyl-4-bromo-5-aminobenzimidazole

HRID 2299152Notes

Reaction equation

HRID 2299152 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:7]=3[N:8]=2)[CH2:3][CH2:2]1.[Br:14]Br>CC(O)=O>[CH:1]1([C:4]2[NH:5][C:6]3[C:12]([Br:14])=[C:11]([NH2:13])[CH:10]=[CH:9][C:7]=3[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24408BromineHCID 183798632-cyclopropyl-1H-benzimidazol-5-amine

Product 1

HCID 1785073302-Cyclopropyl-4-bromo-5-aminobenzimidazoleYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 0.87 g (4.9 mmol) of 2-cyclopropyl-5-aminobenzimidazole in 50 ml of AcOH was added 0.10 ml (1.9 mmol) of Br2 dropwise and resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was concentrated in vacuo and purified on silica gel column chromatography (5% MeOH/EtOAC) to yield 0.42 g (1.8 mmol, >95%) of the desired product.

Workup

  1. customresulting
  2. customreaction mixture
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified on silica gel column chromatography (5% MeOH/EtOAC)

Sources & evidence

ORD record
ord-7b644f429e1b453e8d8a2b0f46f34441
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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