N-bromobutanimide → 2-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

HRID 1921820ノート

反応式

HRID 1921820 の反応式
[S:1]1[C:5]2[C:6](=[O:9])[NH:7][CH2:8][C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:17])C(=O)C1>C(#N)C>[Br:17][C:2]1[S:1][C:5]2[C:6](=[O:9])[NH:7][CH2:8][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 205428054H,5H,6H-thieno[2,3-c]pyrrol-6-one

生成物 1

HCID 590231412-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4,5-Dihydro-thieno[2,3-c]pyrrol-6-one (0.365 g, 2.63 mmol) is dissolved in acetonitrile (10 mL), and NBS (0.47 g, 2.63 mmol) is slowly added at −10° C. The reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue taken-up in EtOAc and washed with 1M NaOH. The organic phase is dried over MgSO4, filtered and concentrated in vacuo. The crude is purified by silica gel column chromatography eluting with a 50:50 mixture and then 50:70 petroleum ether-EtOAc. The title compound is isolated (91.1 mg, 16%). HPLC (254 nm): Rt 2.55 min (70.3%), m/z 218/220 (M+H)+.

後処理

  1. customThe solvent is removed in vacuo
  2. washthe residue taken-up in EtOAc and washed with 1M NaOH
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude is purified by silica gel column chromatography
  7. washeluting with a 50:50 mixture

出典と根拠

ORDレコード
ord-25f33f57b63b40c392bd8ad9b5d2e7da
出典データセット
uspto-grants-2012_05
特許番号
US08173656B2

反応ノート

読み込み中…