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

HRID 1366194ノート

反応式

HRID 1366194 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-96a3a023e9c84c7d9e8dc61d2328b22c
出典データセット
uspto-grants-2011_02
特許番号
US07893058B2

反応ノート

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