Reaction #2161249

ord-e8dfc7a1f2e34383acc4d6b4d36e9118

Reaction equation

CCOC(=O)c1ncc[nH]1
ethyl imidazole-2-carboxylate
O=[N+]([O-])O
nitric acid
→
CCOC(=O)c1nc([N+](=O)[O-])c[nH]1
Ethyl 4-nitro-1H-imidazole-2-carboxylate

Reactants

CCOC(=O)c1ncc[nH]1
ethyl imidazole-2-carboxylate
O=[N+]([O-])O
nitric acid

Reagents

None

Solvents

—
ice water
—
concentrated sulpfuric acid

Conditions

Temperature
55°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureafter cooling
  2. 2
    FiltrationThe precipitated crystals are collected by suction filtration
  3. 3
    Washwashed with 1500 ml of ice-water

Procedure

While cooling on ice, 16.08 g (114.7 mmol) of ethyl imidazole-2-carboxylate are dissolved in 71.7 ml of concentrated sulpfuric acid. 71.7 ml of 100% fuming nitric acid are then added dropwise. The reaction solution is stirred at 50 to 60° C. for 3 h and, after cooling, poured onto 800 ml of an ice/water mixture. The precipitated crystals are collected by suction filtration and washed with 1500 ml of ice-water.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07919489B2uspto-grants-2011_04