Water → 5-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione

HRID 4391Notes

Reaction equation

HRID 4391 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][C:9]1[O:10][C:11]([CH3:32])=[C:12]([CH:14]([OH:31])[CH2:15][O:16][C:17]2[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=2)[N:13]=1.O>CS(C)=O>[CH3:8][C:9]1[O:10][C:11]([CH3:32])=[C:12]([C:14](=[O:31])[CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=2)[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 137139175-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione

Product 1

HCID 137139355-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedioneYield 48.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Acetic anhydride (1.0 ml) was added to a solution of 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (0.5 g) in dimethylsulfoxide (10 ml), and the mixture was allowed to stand overnight and poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concetrated. The oily residue was chromatographed on a column of silica gel (40 g), and from the fractions eluted with benzene-acetone (9:1 V/v), there was obtained 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione (0.24 g, 48.3%). Recrystallization from ethyl acetate-hexane afforded colorless plates, m.p. 161°-162° C. Elemental analysis for C17H16N2O5S, Calcd.: C, 56.66; H, 4.47; N, 7.77. Found: C, 56.62; H, 4.38; N, 7.60.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe oily residue was chromatographed on a column of silica gel (40 g)
  5. washfrom the fractions eluted with benzene-acetone (9:1 V/v)

Sources & evidence

ORD record
ord-d519b00c7e994e338826daf4aa407bae
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

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