Hydrogen Bromide → 2-Bromo-4-nitro-1H-imidazole

HRID 1042953Notes

Reaction equation

HRID 1042953 reaction equation
[BrH:1].[N+]([C:5]1[NH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[N:9]=1)([O-])=O.C(=O)([O-])O.[Na+]>CC1C=CC(C)=CC=1>[Br:1][C:5]1[NH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 178526857HCID 178526857, compound

Product 1

HCID 477542-Bromo-4-nitro-1H-imidazoleYield 47.6%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

2033.5 g of 49 mass % hydrobromic acid was added dropwise to 145.6 g of 2,4-dinitroimidazole wetted with p-xylene (wetted with 12 mass % of p-xylene). The temperature of the reaction liquid was elevated to 100° C. and reacted for 5 hours. After the reaction ended, the reaction liquid was gradually neutralized with 2000 mL of a saturated sodium hydrogen carbonate aqueous solution while the solution was cooled to deposit crystals. After the crystals were filtered, the crystals were heated and dissolved in 3000 mL of water at 95° C. and 75.0 g of 2-bromo-4-nitroimidazole (yield 47.6%) (HPLC purity 100%) was obtained by cooling, filtration and drying. This was identified to be 2-bromo-4-nitroimidazole by

Workup

  1. customThe temperature of the reaction liquid
  2. customwas elevated to 100° C.
  3. customreacted for 5 hours
  4. customthe reaction liquid
  5. temperaturewas cooled
  6. filtrationAfter the crystals were filtered
  7. temperaturethe crystals were heated
  8. dissolutiondissolved in 3000 mL of water at 95° C.

Sources & evidence

ORD record
ord-c17a838584224dfcb3bb81f7495cf78b
Source dataset
uspto-grants-2013_10
Patent number
US08558005B2

Reaction notes

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