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

HRID 1921820노트

반응식

HRID 1921820 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-25f33f57b63b40c392bd8ad9b5d2e7da
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173656B2

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