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

HRID 1936578Notes

Reaction equation

HRID 1936578 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 1 g of 4,7-dimethylbenzimidazole in 8 mL of concentrated sulfuric acid 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 magnesium sulfate 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 magnesium sulfate
  3. customrotary evaporated

Sources & evidence

ORD record
ord-d391e17b85d5422ab93bed731ded3303
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

Loading…