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

HRID 973689

반응식

HRID 973689 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 521998p-Toluenesulfonic acid monohydrate촉매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-cd531bdaa9564741b2db055e2785f4e3
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064849

연결된 노트

불러오는 중…