Imidazole → 2-(1-imidazolyl)-4-nitro-1H-benzimidazole

HRID 429652Notes

Reaction equation

HRID 429652 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=2[N:3]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>CN1CCCC1=O.[Cl-].[Na+].O>[N:14]1([C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=3[N:3]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 14765451HCID 14765451, compound

Product 1

HCID 183553122-(1-imidazolyl)-4-nitro-1H-benzimidazoleYield 50.3%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-4-nitro-1H-benzimidazole (300 mg) in N-methyl-2-pyrrolidone (4 ml) was added imidazole (517 mg) and the mixture was stirred at 80° C. for 8 hours. The reaction mixture was poured into brine and extracted with a mixture of chloroform and methanol. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (100-0−30-1) to give 2-(1-imidazolyl)-4-nitro-1H-benzimidazole (175 mg).

Workup

  1. extractionextracted with a mixture of chloroform and methanol
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (100-0−30-1)

Sources & evidence

ORD record
ord-3060fc3a49bb4dab876e43f3a0b4d77f
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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