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

HRID 2260729Notes

Reaction equation

HRID 2260729 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-16c94c0961064ff9a2097851361ca9b1
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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