Nitric Acid → 1-Methyl-3-(1-methyl-4-nitro-1h-pyrazol-3-yl)-2-imidazolidinone

HRID 632798Notes

Reaction equation

HRID 632798 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=2)[C:3]1=[O:13].[N+:14]([O-])([OH:16])=[O:15].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]([CH3:12])[N:8]=2)[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 1180613691-Methyl-3-(1-methyl-1h-pyrazol-3-yl)-2-imidazolidinone

Product 1

HCID 1180612191-Methyl-3-(1-methyl-4-nitro-1h-pyrazol-3-yl)-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 1-methyl-3-(1-methyl-1H-pyrazol-3-yl)imidazolidin-2-one (161 mg) in acetic anhydride (2.1 mL) was added fuming nitric acid (0.074 mL) under ice-cooling, and the mixture was stirred for 1.5 hr under ice-cooling. The reaction mixture was poured into ice water, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (101 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-5bd75cf6a94e40e9885d8fbde95790c2
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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