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

HRID 1925207ノート

反応式

HRID 1925207 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 962Water溶媒

反応条件

温度
135 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7ecaa6005e1641c99d7773d0ea03a517
出典データセット
uspto-grants-2012_05
特許番号
US08178672B2

反応ノート

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