Ethanol → 2-((2-Nitro-1H-imidazol-1-yl)methoxy)-1,3-propanediol

HRID 2166350

Reaction equation

HRID 2166350 reaction equation
C([O:4][CH2:5][CH:6]([CH2:17][O:18]C(=O)C)[O:7][CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[N+:14]([O-:16])=[O:15])(=O)C.C(O)C.[O-]CC.[Na+]>CO>[OH:18][CH2:17][CH:6]([CH2:5][OH:4])[O:7][CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 156234161-[2-Acetoxy-1-(acetoxymethyl)ethoxy]methyl-2-nitroimidazol2×

Product 1

HCID 1291462-((2-Nitro-1H-imidazol-1-yl)methoxy)-1,3-propanediolYield 130.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.01 g of 1-[2-acetoxy-1-(acetoxymethyl)ethoxy]-methyl-2-nitroimidazol (compound (1)) was dissolved in 50 ml of absolute methanol, and stirred at room temperature while being added with 5% absolute ethanol solution of sodium ethoxide dropwise until pH reached 9.0. Stirred at room temperature over 3 hours. Then Dowex 50 W (H+, made by Dow Chemical) was slowly added until the liquid had a pH of 7.0. Dowex 50 W was removed by suction filtration, and the solvent was distilled off under reduced pressure. The residue was subjected to recrystallization by ethanol to obtain 2.83 g of the title compound as light yellow needles (yield: 94%).

Workup

  1. stirringStirred at room temperature over 3 hours
  2. additionThen Dowex 50 W (H+, made by Dow Chemical) was slowly added until the liquid
  3. customDowex 50 W was removed by suction filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was subjected to recrystallization by ethanol

Sources & evidence

ORD record
ord-f987d57e40684379a2d397270d96a499
Source dataset
uspto-grants-1990_07
Patent number
US04945102

Linked notes

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