Acetic Acid → 4-amino-2-[2-(dimethylamino)-ethylamino]-1H-benzimidazole

HRID 2298811Notes

Reaction equation

HRID 2298811 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][NH:5][C:6]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-])=O)[C:8]=2[N:7]=1.C(O)(=O)C>C(O)C.[Fe]>[NH2:15][C:14]1[C:8]2[N:7]=[C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:18])[CH3:1])[NH:10][C:9]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 183786772-[2-(dimethylamino)ethylamino]-4-nitro-1H-benzimidazole

Product 1

HCID 183785624-amino-2-[2-(dimethylamino)-ethylamino]-1H-benzimidazoleYield 86.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[2-(dimethylamino)ethylamino]-4-nitro-1H-benzimidazole (105 mg) in ethanol (4 ml) were added iron (reduced, 118 mg) and acetic acid (0.24 ml) at room temperature and the mixture was refluxed for 6 hours. The precipitate was filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in a mixture of chloroform and methanol (5-1) and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over magnesium sulfate. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol-ammonia solution (28%)=160-32-1) to give 4-amino-2-[2-(dimethylamino)-ethylamino]-1H-benzimidazole (80 mg).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of chloroform and methanol (5-1)
  5. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol-ammonia solution (28%)=160-32-1)

Sources & evidence

ORD record
ord-33439590b31344f0888e289ad4ded073
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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