2-Nitroimidazole → 1-[2-Acetoxy-1-(acetoxymethyl)ethoxy]methyl-2-nitroimidazol

HRID 2166349Notes

Reaction equation

HRID 2166349 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[C:9]([O:12][CH2:13][CH:14]([O:20][CH2:21]OC(=O)C)[CH2:15][O:16][C:17](=[O:19])[CH3:18])(=[O:11])[CH3:10]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:9]([O:12][CH2:13][CH:14]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:20][CH2:21][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 107012-NitroimidazoleHCID 97948881,3-Propanediol, 2-((acetyloxy)methoxy)-, 1,3-diacetate

Product 1

HCID 156234161-[2-Acetoxy-1-(acetoxymethyl)ethoxy]methyl-2-nitroimidazolYield 89.1%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

5.6 g of 2-nitroimidazol, 12.4 g of 1,3-diacetoxy-2-acetoxymethoxypropane and 0.5 g of p-toluenesulfonic acid monohydrate were placed in a flask connected with a trap for reducing pressure by an aspirator. The flask was heated by oil bath of 130°-140° C. under reduced pressure while stirred. Acetic acid was distilled out as the reaction proceeded. In about 15 minutes, the reaction was completed. After cooling down to room temperature, the content was added with about 300 ml ethyl acetate and subjected to extraction. The extract was washed with saturated aqueous sodium hydrogen carbonate, and with water in this order. Then it was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by separable high performance liquid chromatography through silica gel columns using a mixture solvent (ethyl acetate - benzene) as an eluate to obtain 13.3 g of the title compound as a viscous oil material (yield: 88.6%).

Workup

  1. customconnected with a trap
  2. temperatureThe flask was heated by oil bath of 130°-140° C. under reduced pressure
  3. distillationAcetic acid was distilled out as the reaction
  4. additionthe content was added with about 300 ml ethyl acetate
  5. extractionsubjected to extraction
  6. washThe extract was washed with saturated aqueous sodium hydrogen carbonate
  7. dry with materialThen it was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by separable high performance liquid chromatography through silica gel columns

Sources & evidence

ORD record
ord-d48821d144c74becaa0911aa1dab4de3
Source dataset
uspto-grants-1990_07
Patent number
US04945102

Reaction notes

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