Reaction #2161253

ord-b793f13c47284608a67f50fde8aaafc1

Reaction equation

C1CCCCC1.CCOC(C)=O
cyclohexane ethyl acetate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CI
iodomethane
CCOC(=O)c1nc([N+](=O)[O-])c[nH]1
ethyl 4-nitro-1H-imidazole-2-carboxylate
→
CCOC(=O)c1nc([N+](=O)[O-])cn1C
Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate

Reactants

C1CCCCC1.CCOC(C)=O
cyclohexane ethyl acetate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CI
iodomethane
CCOC(=O)c1nc([N+](=O)[O-])c[nH]1
ethyl 4-nitro-1H-imidazole-2-carboxylate

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling
  2. 2
    Filtrationthe mixture is filtered
  3. 3
    Washthe residue is washed with dichloromethane
  4. 4
    OtherThe solid obtained
  5. 5
    Otheris dried in vacuo

Procedure

6.80 g (36.7 mmol) of ethyl 4-nitro-1H-imidazole-2-carboxylate are dissolved in 140 ml of acetone, and 11.2 g (80.8 mmol) of potassium carbonate and 4.57 ml (73.5 mmol) of iodomethane are added. The mixture is then stirred at 60° C. for 4 h. According to TLC (cyclohexane/ethyl acetate 2:1), the starting material has been converted completely. After cooling, the mixture is filtered, the residue is washed with dichloromethane and the filtrate is freed from the solvent. The solid obtained is dried in vacuo.

Source

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