Acetylacetone → 2-Methyl-4-nitro-1H-benzo[d]imidazole

HRID 1864973Notes

Reaction equation

HRID 1864973 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11])([O-:3])=[O:2].[CH3:12][C:13](=O)CC(=O)C>C(O)C.Cl>[CH3:12][C:13]1[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=2[N:11]=1

Participants

5

Reactant 2

HCID 31261AcetylacetoneHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 15126612-Methyl-4-nitro-1H-benzo[d]imidazoleYield 95.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Nitrobenzene-1,2-diamine (1.0 g) was dissolved in ethanol (90 mL) and 5N hydrochloric acid (24 mL), and to this solution was added 2,4-pentanedione (1.3 g). The mixture was heated for 3 hours under reflux, cooled down to room temperature and concentrated. To this concentrate was added ethyl acetate, and the mixture was washed successively with saturated aqueous sodium bicarbonate and water, and dried over sodium sulfate to give the title compound (1.1 g).

Workup

  1. temperatureThe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. concentrationconcentrated
  4. additionTo this concentrate was added ethyl acetate
  5. washthe mixture was washed successively with saturated aqueous sodium bicarbonate and water
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-07dc22c64457410986f0c45cf8204f69
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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