Acetic Acid → 1,4-Dinitro-1H-imidazole

HRID 1042951Notes

Reaction equation

HRID 1042951 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(O)(=O)C.[N+:13]([O-])([OH:15])=[O:14].C(OC(=O)C)(=O)C>O>[N+:13]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric Acid2×HCID 7918Acetic AnhydrideHCID 178526856HCID 178526856, compound

Product 1

HCID 51694961,4-Dinitro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 20 g of 4-nitroimidazole was put in a flask, 36.4 mL of acetic acid was added thereto and while the temperature of the reaction solution was kept below 20° C., 14.6 mL of 97 mass % nitric acid was added dropwise thereto. After the dropwise addition of nitric acid was completed, 36.4 mL of acetic anhydride was added dropwise thereto and after the temperature of the reaction solution elevated to 25° C., the resultant mixture was allowed to react for 3 hours. After the reaction ended, the reaction solution was added into 100 g of iced water. Extraction with 100 mL of p-xylene was performed four times and this organic layer was washed twice with 100 mL of a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and 30 g of magnesium sulfate was added thereto for dehydration to obtain 1,4-dinitroimidazole as a p-xylene solution. Subsequently, the solvent was evaporated with an evaporator to about two third amount, and the solution was heated to 125° C. and allowed to react for 24 hours so as to perform conversion to 2,4-dinitroimidazole. After the reaction ended, the deposited solid was filtered to obtain 24.1 g of 2,4-dinitroimidazole as a solid wetted with p-xylene (wetted with 15 mass % of p-xylene, yield 74.9%). This was identified to be 2,4-dinitroimidazole by

Workup

  1. customwas kept below 20° C.
  2. customelevated to 25° C.
  3. customto react for 3 hours
  4. extractionExtraction with 100 mL of p-xylene
  5. washthis organic layer was washed twice with 100 mL of a saturated sodium hydrogen carbonate aqueous solution
  6. customThe organic layer was separated
  7. addition30 g of magnesium sulfate was added

Sources & evidence

ORD record
ord-0b579937f8a847ed83b7e121410b0fe2
Source dataset
uspto-grants-2013_10
Patent number
US08558005B2

Reaction notes

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