Thiazolidinedione → 5-{4-[2-(2-Methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione

HRID 1873821노트

반응식

HRID 1873821 반응식
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[S:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27].N1CCCCC1>CCO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:2](=[O:1])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][CH:25]2[S:21][C:22](=[O:27])[NH:23][C:24]2=[O:26])=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 866450774-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehyde

생성물 1

HCID 252303365-{4-[2-(2-Methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione수율 80.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirring solution of 4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehyde (1.71 g, 6.28 mmol) in absolute EtOH (50 ml) was added 2,4-thiazolidinedione (0.81 g, 6.91 mmol) and piperidine (0.68 mL, 6.9 mmol), and the resulting solution was heated to reflux. The reaction was refluxed overnight and then evaporated in vacuo. The residue was dissolved in EtOAc and this solution was washed with aqueous HOAc (pH 5-6), brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel eluting with 20-40% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 1.87 g (80%) of the title compound as a light yellow solid. MS (ESI−) for C19H17NO5S m/z 370.1 (M−H)−.

후처리

  1. temperaturethe resulting solution was heated to reflux
  2. temperatureThe reaction was refluxed overnight
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washthis solution was washed with aqueous HOAc (pH 5-6), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customchromatographed on silica gel eluting with 20-40% EtOAc/DCM
  10. additionFractions containing product
  11. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a37800e335bb4b43b196358810c5ca01
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304441B2

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