(2-Oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzene-1-sulfonate → (1,3-Oxazolidin-2-on-4-yl)methyl Thioacetate

HRID 622631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622631
C1(C)C=CC(S([O:10][CH2:11][CH:12]2[CH2:16][O:15][C:14](=[O:17])[NH:13]2)(=O)=O)=CC=1.[C:19]([O-])(=[S:21])[CH3:20].C([N+](CCCC)(CCCC)CCCC)CCC>CC(C)=O>[C:19]([O:10][CH2:11][CH:12]1[CH2:16][O:15][C:14](=[O:17])[NH:13]1)(=[S:21])[CH3:20]

Komponenten

4

Edukt 2

HCID 14456891(2-Oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzene-1-sulfonateHCID 178477078HCID 178477078, Verbindung

Produkt 1

HCID 21291365(1,3-Oxazolidin-2-on-4-yl)methyl ThioacetateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 2-oxo-1,3-oxazolidin-4-ylmethyl p-toluenesulfonate (1.22 g., 0.0045 mole) and tetrabutylammonium thioacetate (1.71 g, 0.0054 mole) in 75 ml. acetone was refluxed under nitrogen for 90 min. The reaction mixture was concentrated to dryness and the residue was chromatographed on silica gel (250 g). Elution with 4:1 ethyl acetate-hexane yielded 580 mg. of the title compound (75% yield). NMR (CDCl3): 2.38 (s, 3H); 3.06 (d, 2H); 3.84-4.67 (c, 3H); and 6.3 (b, 1H)ppm.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was chromatographed on silica gel (250 g)
  3. washElution with 4:1 ethyl acetate-hexane
  4. customyielded 580 mg

Quellen und Nachweise

ORD-Eintrag
ord-aed4ffe41a6e4aa181c5b3b60ce684b9
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04772597

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