Water → 5-({4-[2-(5-Acetylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

HRID 1756626Notes

Reaction equation

HRID 1756626 reaction equation
C(OC(=O)C)(=O)C.[OH:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)=[N:15][CH:16]=1)[CH3:10].O>CS(C)=O>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)=[N:15][CH:16]=1)(=[O:8])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 4147757Leriglitazone

Product 1

HCID 52014465-({4-[2-(5-Acetylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Acetic anhydride (25 ml) was added to a solution of 5-[4-[2-[5-(1-hydroxyethyl)-2-pyridyl]ethoxy]benzyl]-2,4-thiazolidinedione (8.7 g) in dimethyl sulfoxide (100 ml). The mixture was allowed to stand at room temperature for 4 days. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue was subjected to silica gel column chromatography. A fraction eluted with chloroform-methanol (100:1, v/v) gave 5-[4-[2-(5-acetyl-2-pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione. This compound was recrystallized from ethanol to obtain colorless prisms, m.p. 114°-115° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washA fraction eluted with chloroform-methanol (100:1

Sources & evidence

ORD record
ord-a73f06e4e64b4d2cac4188d39ca36b6c
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

Loading…