Nitric Acid → Ethyl 1-methyl-4-nitroimidazole-2-carboxylate

HRID 1857071Notes

Reaction equation

HRID 1857071 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH3:1][N:2]1[CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[N:4]=[C:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4261883ethyl 1-methyl-1H-imidazole-2-carboxylate

Product 1

HCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 1-methylimidazole-2-carboxylate was carefully dissolved in 1000 mL of concentrated sulfuric acid cooled to 0° C. 90% nitric acid (1 L) was slowly added maintaining a temperature of 0° C. The reaction was then refluxed with an efficient condenser (-20° C.) in a well ventilated hood for 50 min. The reaction was cooled with an ice bath, and quenched by pouring onto 10 L ice. The resulting blue solution was then extracted with 20 L DCM, the combined extracts dried (sodium sulfate) and concentrated in vacuo to yield a tan solid which was recrystallized from 22 L of 21:1 carbon tetrachloride/ethanol. The resulting white crystals are collected by vacuum filtration.

Workup

  1. temperaturemaintaining a temperature of 0° C
  2. temperatureThe reaction was then refluxed with an efficient condenser (-20° C.) in a well ventilated hood for 50 min
  3. temperatureThe reaction was cooled with an ice bath
  4. customquenched
  5. additionby pouring onto 10 L ice
  6. extractionThe resulting blue solution was then extracted with 20 L DCM
  7. dry with materialthe combined extracts dried (sodium sulfate)
  8. concentrationconcentrated in vacuo
  9. customto yield a tan solid which
  10. customwas recrystallized from 22 L of 21:1 carbon tetrachloride/ethanol
  11. filtrationThe resulting white crystals are collected by vacuum filtration

Sources & evidence

ORD record
ord-cd65763fa02d4b8aa075484bb29d49a2
Source dataset
uspto-grants-2000_11
Patent number
US06143901

Reaction notes

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