Nitric Acid → 2,4-Dimethyl-5-nitro-1H-imidazole (9CI)

HRID 2118539Notes

Reaction equation

HRID 2118539 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[NH:8][CH:9]=[C:10]([CH3:12])[N:11]=1.NC(N)=O.[N+:17]([O-])([OH:19])=[O:18]>>[CH3:6][C:7]1[NH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([CH3:12])[N:11]=1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1176UreaHCID 178430880HCID 178430880, compound

Product 1

HCID 1355544302,4-Dimethyl-5-nitro-1H-imidazole (9CI)Yield 67.5%

Conditions

Temperature
200 °C

Procedure

Sulfuric acid (30 ml, 0.56 mole) was added dropwise to 2,4-dimethylimidazole (10 g, 0.104 mole), and urea (6.24 g, 0.104 mole), in a 1 l. flask cooled in ice. This was followed by the addition of fuming nitric acid (30 ml, 0.72 mole). When all had been added, the flask was heated at 200° C. for 1-2 minutes, whereupon a vigorous reaction ensued, necessitating the removal of the heat. When the reaction subsided, heating is continued for 10 minutes. The flask was then allowed to cool, and the reaction mixture was added to 300 ml of H2O. The solution was adjusted to pH 5 with aqueous sodium hydroxide (about 40 g of sodium hydroxide was required). The resulting precipitate was filtered off and dried in vacuum to give 9.9 g of 2,4-dimethyl-5-nitroimidazole.

Workup

  1. temperatureflask cooled in ice
  2. additionWhen all had been added
  3. customthe removal of the heat
  4. temperatureheating
  5. temperatureto cool
  6. additionthe reaction mixture was added to 300 ml of H2O
  7. filtrationThe resulting precipitate was filtered off
  8. customdried in vacuum

Sources & evidence

ORD record
ord-0386aadd76b14b0ab41165203615ed01
Source dataset
uspto-grants-1987_07
Patent number
US04678799

Reaction notes

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