Water → 5-(4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

HRID 1595527Notes

Reaction equation

HRID 1595527 reaction equation
[CH3:1][CH:2]([S:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)(=[O:6])=[O:5])[CH3:3].[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].C1(C)C=CC=CC=1.O>N1CCCCC1.C(O)(=O)C.CC(C)=O>[CH3:3][CH:2]([S:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]=[C:29]3[S:25][C:26](=[O:31])[NH:27][C:28]3=[O:30])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1)(=[O:6])=[O:5])[CH3:1]

Participants

8

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 5437ThiazolidinedioneHCID 21705008HCID 21705008, compound

Product 1

HCID 867573785-(4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dioneYield 58.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 180AcetoneSolvent

Procedure

1.4 g (4 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl 2-propanesulfonate, 0.94 (8 mmole) 2,4-thiazolidinedione, 5 drops of piperidine, 6 drops of acetic acid and toluene were refluxed with water separation in a Dean-Stark apparatus. When the starting material was consumed the heat was removed and the formed crystals were recrystallized in water:acetone to give 1.5 g (yield 58.6%) of 5-(4-[2-(4-(2-propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. customWhen the starting material was consumed the heat
  2. customwas removed
  3. customthe formed crystals were recrystallized in water

Sources & evidence

ORD record
ord-c55b2f353c3445c58d1496bff4d4a962
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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