1,2-Epoxybutane → HCID 18465119, compound

HRID 2230067Notes

Reaction equation

HRID 2230067 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.[O:10]1[CH:12]([CH2:13][CH3:14])[CH2:11]1>C(O)=O>[OH:10][CH:12]([CH2:13][CH3:14])[CH2:11][N:3]1[C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=[C:2]1[CH3:1]

Participants

4

Reactant 2

HCID 78341,2-EpoxybutaneHCID 127602-Methyl-5-nitroimidazole

Product 1

HCID 18465119HCID 18465119, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
10 °C

Procedure

The reaction mixture of 2-methyl -5-nitroimidazole (127 g, 1.0 mol) and 88% formic acid will be cooled to 10° C. under stir, then 1,2-epoxybutane (360 g, 5.0 mol) will be added dropwise to above cold solution under the condition of 10° C. After the dropping, the reactants will be placed at room temperature overnight. The formic acid will be recovered under reduced pressure. To this residue, 100 ml of water will be added. The mixture will be filtered and the filter residue will be washed with water. The water phases will be combined, alkalified with 10 M sodium hydroxide aqueous solution up to pH 9. The solution will be placed in the cold room overnight for crystallization. The crystals will be collected, washed with water, and then dried. Crude product will be recrystallized from toluene to give 1-(2-hydroxybutyl)-2-methyl-5-nitro-1H-imidazole.

Workup

  1. customThe formic acid will be recovered under reduced pressure
  2. additionTo this residue, 100 ml of water will be added
  3. filtrationThe mixture will be filtered
  4. washthe filter residue will be washed with water
  5. customThe solution will be placed in the cold room overnight for crystallization
  6. customThe crystals will be collected
  7. washwashed with water
  8. customdried
  9. customCrude product will be recrystallized from toluene

Sources & evidence

ORD record
ord-8ba479bd497e482f9c364af5a7bca312
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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