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

HRID 973689

反応式

HRID 973689 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 521998p-Toluenesulfonic acid monohydrate触媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cd531bdaa9564741b2db055e2785f4e3
出典データセット
uspto-grants-1991_11
特許番号
US05064849

関連ノート

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