Thiazolidinedione → 5-(4-[2-(4-Methanesulfonylaminophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

HRID 1595499노트

반응식

HRID 1595499 반응식
[CH:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)=O.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C([O-])(=O)C.[Na+]>O.CC(C)=O>[CH3:20][S:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][O:7][C:6]2[CH:21]=[CH:22][C:3]([CH:1]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])=[CH:4][CH:5]=2)=[CH:11][CH:12]=1)(=[O:19])=[O:18]

참가 물질

5

반응물 3

HCID 5437ThiazolidinedioneHCID 517045Sodium AcetateHCID 21704959N-{4-[2-(4-formylphenoxy)ethyl]phenyl}methanesulfonamide

생성물 1

HCID 536511465-(4-[2-(4-Methanesulfonylaminophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione수율 40%

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

반응 조건

온도
140 °C

실험 절차

1.6 g (5 mmole) N-{4-[2-(4-formylphenoxy)ethyl]phenyl}methanesulfonamide, 0.73 g (6.25 mmole) 2,4-thiazolidinedione and 1.025 g (12.5 mmole) sodium acetate were mixed and heated to 140° C. on an oil bath under vacuum (it melted at 130° C.). It was kept at 140° C. for 20 minutes and thereafter taken off the heat. When the temperature was low enough water:acetone (2:1) was added to dissolve the reaction product. Acetone was evaporated in vacuo, acetic acid was added and the obtained crystals were filtered off and recrystallized in dichloromethane to give 0.83 g (yield 40%) of 5-(4-[2-(4-methanesulfonylamino-phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

후처리

  1. additionwas added
  2. dissolutionto dissolve the reaction product
  3. customAcetone was evaporated in vacuo, acetic acid
  4. additionwas added
  5. filtrationthe obtained crystals were filtered off
  6. customrecrystallized in dichloromethane

출처 및 근거

ORD 기록
ord-e579b35d72b446908cbc71d33aa59962
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288096B1

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