Azobisisobutyronitrile → HCID 22258788、化合物

HRID 1611121ノート

反応式

HRID 1611121 の反応式
[N+:1]([C:4]1[C:13]2[CH2:12][O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].BrN1[C:19](=[O:20])[CH2:18]CC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[O-]CC.[Na+]>C(Cl)(Cl)(Cl)Cl.C(O)C>[CH2:19]([O:20][CH:12]1[C:13]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=2[O:9][CH2:10][O:11]1)[CH3:18]

参加物

7

反応物 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2723922Sodium ethoxideHCID 33256175-nitro-4H-1,3-benzodioxine

生成物 1

HCID 22258788HCID 22258788、化合物収率 87%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 5-nitro-4H-1,3-benzodioxine (10.0 g, 55.203 mmol) in carbon tetrachloride (70 mL) were added N-bromosuccinimide (10.808 g, 60.723 mmol) and 2,2′-azobisisobutyronitrile (0.906 g, 5.520 mmol). The mixture was stirred at 100° C. for 2 hrs. After cooled to room temperature, a solution of sodium ethoxide (4.884 g, 71.764 mmol) in ethanol (70 mL) was added to the mixture, and the stirring was continued at room temperature for 3 hrs. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give 4-ethoxy-5-nitro-4H-1,3-benzodioxine as a pale yellow oil (10.8 g, yield; 87%).

後処理

  1. temperatureAfter cooled to room temperature
  2. waitthe stirring was continued at room temperature for 3 hrs
  3. customThe reaction was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)

出典と根拠

ORDレコード
ord-a86d060e81ba484aa5b4c227204081de
出典データセット
uspto-grants-2006_01
特許番号
US06984649B1

反応ノート

読み込み中…