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

HRID 4391
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 4391
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
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Komponenten

5

Edukt 3

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

Produkt 1

HCID 137139355-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedioneAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d519b00c7e994e338826daf4aa407bae
Quelldatensatz
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04725610

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