Nitric Acid → HCID 118061496, compound

HRID 632811Notes

Reaction equation

HRID 632811 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][N:6]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]2=[O:23])=[N:7]1.[OH-].[Na+]>C(OC(=O)C)(=O)C.O>[CH3:5][N:6]1[CH:10]=[C:9]([N+:1]([O-:4])=[O:2])[C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:12]2=[O:23])=[N:7]1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 118060737HCID 118060737, compound

Product 1

HCID 118061496HCID 118061496, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent2×

Procedure

To acetic anhydride (30 mL) was added fuming nitric acid (3.77 mL) under ice-cooling, and the mixture was stirred for 5 min. The obtained solution was added dropwise to a solution of tert-butyl 3-(1-methyl-1H-pyrazol-3-yl)-2-oxoimidazolidine-1-carboxylate (12.1 g) in acetic anhydride (60 mL) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with water, and the mixture was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and 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 (NH, ethyl acetate/hexane) to give the title compound (11.3 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at 0° C. for 30 min
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a27ac4ad14a34afe9f3df77a3205305e
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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