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

HRID 1595499ノート

反応式

HRID 1595499 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e579b35d72b446908cbc71d33aa59962
出典データセット
uspto-grants-2001_09
特許番号
US06288096B1

反応ノート

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