N-bromobutanimide → 7-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1521574ノート

反応式

HRID 1521574 の反応式
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].[Br:13]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:13][C:10]1[CH:9]=[CH:8][C:7]2[NH:1][C:2](=[O:12])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:11]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

生成物 1

HCID 149781117-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the title compound from Example 2 Step B (17.0 g, 106 mmol) in N,N-dimethylformamide (500 mL) was added N-bromosuccinimide (25.2 g, 141 mmol) at room temperature, and then the mixture was refluxed for 16 hours. The reaction mixture was diluted with ethyl acetate (1 L), and the separated organic layer was washed with 0.1 M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over Na2SO4, filtered and concentrated. Purification by flash chromatography on silica gel (petroleum ether:ethyl acetate=12:1 to 3:1) provided a crude product that was recrystallized from ethyl acetate and petroleum ether (v:v=1:10) to give the title compound: LCMS m/z=241 [M+2+H]+. 1H NMR (400 MHz, d6-DMSO): δ 9.56 (s, 1H), 7.46 (s, 1H), 7.37 (d, J=8.4 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 2.65 (m, 2H), 2.12-2.07 (m, 4H).

後処理

  1. temperaturethe mixture was refluxed for 16 hours
  2. washthe separated organic layer was washed with 0.1 M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (petroleum ether:ethyl acetate=12:1 to 3:1)
  7. customprovided a crude product that
  8. customwas recrystallized from ethyl acetate and petroleum ether (v:v=1:10)

出典と根拠

ORDレコード
ord-d381ec2eff0d467891f37d4bd14e601f
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

読み込み中…