Acetic Anhydride → 1-[6-(2-Chlorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone

HRID 1925207노트

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HRID 1925207 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[N:14]([CH:15]=1)[CH:13]=[CH:12][O:11]2.[C:16](OC(=O)C)(=[O:18])[CH3:17]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[N:14]([C:15]=1[C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][O:11]2

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 576729966-(2-Chlorophenyl)-imidazo[2,1-b]oxazole

생성물 1

HCID 576729731-[6-(2-Chlorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone수율 83%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 962Water용매

반응 조건

온도
135 °C

실험 절차

To a mixture of 6-(2-chlorophenyl)-imidazo[2,1-b]oxazole (1.0 g, 4.57 mmol) and acetic anhydride (23 ml) is added 3 drops of concentrated sulfuric acid. The reaction mixture is heated at 135° C. for 1 hour. The reaction mixture is then poured onto 50 ml of ice, and diluted with 100 ml of water and the resulting mixture is extracted three times with 75 ml each of ethyl acetate. The combined extracts are dried with magnesium sulfate, filtered and concentrated in vacuo, to give a brown oil. The product is purified by flash chromatography on silica gel (hexane/ethyl acetate 3:1), yielding 994 mg of an off-white solid (83%). M.p.=121-122° C.; 300 MHz 1H NMR (CDCl3) δ: 8.02 (d, J=1.6 Hz, 1H), 7.56-7.38 (m, 5H), 2.05 (s, 3H). LCMS: 261 [M+H]; calc. for C13H9ClN2O2: C, 59.84; H, 3.48; N, 10.74; found. C, 60.18; H, 3.16; N, 10.61.

후처리

  1. extractionthe resulting mixture is extracted three times with 75 ml each of ethyl acetate
  2. dry with materialThe combined extracts are dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customThe product is purified by flash chromatography on silica gel (hexane/ethyl acetate 3:1)

출처 및 근거

ORD 기록
ord-7ecaa6005e1641c99d7773d0ea03a517
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178672B2

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