Thiazolidinedione → HCID 53906345, compound

HRID 1595506Notes

Reaction equation

HRID 1595506 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1)(=[O:4])=[O:3].[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>C(O)(=O)C.O>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[C:27]2[S:23][C:24](=[O:29])[NH:25][C:26]2=[O:28])=[CH:19][CH:20]=1)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 5437ThiazolidinedioneHCID 517045Sodium AcetateHCID 18366337Propan-2-one--water (1/1)HCID 21705005HCID 21705005, compound

Product 1

HCID 53906345HCID 53906345, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.7 g (5.3 mmole) 2-[2-(4-formylphenoxy)ethyl]phenyl methanesulfonate, 0.77 g (6.6 mmole) 2,4-thiazolidinedione and 1.06 g (13.2 mmole) sodium acetate were heated to 130° C. and allowed to stay at 130° C. for 10 minutes. The reaction mixture was taken off the heat and water:acetone (2:1) was added, the formed solid material was stirred with water and acetic acid, the precipitate was collected by filtration and washed with diethyl ether and recrystallized in dichloromethane to give 1.63 g (yield 61%) of 5-(4-[2-(2-methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. temperatureheat
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with diethyl ether
  4. customrecrystallized in dichloromethane

Sources & evidence

ORD record
ord-3e4e1e73bf514500b5fc77105bfd0b2e
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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