Nitric Acid → 4,7-Dimethyl-5-nitro-1H-benzo[d]imidazole

HRID 1736461Notes

Reaction equation

HRID 1736461 reaction equation
[CH3:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[C:5]([CH3:11])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH3:11][C:5]1[C:6]2[NH:7][CH:8]=[N:9][C:10]=2[C:2]([CH3:1])=[CH:3][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 130708274,7-Dimethyl-1H-benzo[d]imidazole

Product 1

HCID 224622214,7-Dimethyl-5-nitro-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cold (ice bath) solution of 4,7-dimethylbenzimidazole (1 g) in concentrated sulfuric acid (8 mL) is added dropwise concentrated nitric acid (0.37 mL), over 50 minutes. The mixture is stirred an additional 30 minutes in the ice bath, then poured into a mixture of crushed ice (30 mL) and ammonium hydroxide (30 mL). The resulting mixture is extracted with ethyl acetate. The extract is dried over MgSO4 and rotary evaporated to afford 4,7-dimethyl-5-nitrobenzimidazole as a dark tan solid.

Workup

  1. extractionThe resulting mixture is extracted with ethyl acetate
  2. dry with materialThe extract is dried over MgSO4
  3. customrotary evaporated

Sources & evidence

ORD record
ord-1c67992baf2d4755967a5cb2004b6564
Source dataset
uspto-grants-1996_07
Patent number
US05541210

Reaction notes

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