Phosgene → 5-{[(6-Methylpyridin-3-yl)oxy]methyl}-3-(propan-2-yl)-1,3-oxazolidin-2-one

HRID 647978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647978
[C:1](Cl)(Cl)=[O:2].[OH:5][CH:6]([CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH2:7][O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1>C1(C)C=CC=CC=1.O1CCOCC1>[CH:18]([N:17]1[CH2:16][CH:6]([CH2:7][O:8][C:9]2[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[O:5][C:1]1=[O:2])([CH3:20])[CH3:19]

Komponenten

5

Edukt 2

HCID 6371PhosgeneHCID 204834671-[(6-Methylpyridin-3-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

Produkt 1

HCID 204834455-{[(6-Methylpyridin-3-yl)oxy]methyl}-3-(propan-2-yl)-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 10 g of phosgene in 40 ml of toluene is added dropwise at 5°-10° C. to 15.6 g of 3-(2'-hydroxy-3'-isopropylamino-propoxy)-6-methyl-pyridine, dissolved in 75 ml of dioxane, in the presence of 8 ml of 2,6-lutidine,whilst stirring. The reaction mixture is stirred overnight at room temperature and is then evaporated in vacuo. The evaporation residue is rendered alkaline with a little concentrated sodium hydroxide solution and is extracted with 200 ml of ethyl acetate. The organic phase is evaporated, initially at approx. 20 mm Hg and then at 0.1 mm Hg/60° C. bath temperature. Approx. 50 ml of ether are added to the residue which remains, giving crystalline 3-isopropyl-5-[(6-methylpyridin-3-yloxy)methyl]-oxazolidin-2-one of melting point 86°-88° C.

Aufarbeitung

  1. customis then evaporated in vacuo
  2. extractionis extracted with 200 ml of ethyl acetate
  3. customThe organic phase is evaporated, initially at approx. 20 mm Hg
  4. customat 0.1 mm Hg/60° C. bath temperature
  5. additionApprox. 50 ml of ether are added to the residue which

Quellen und Nachweise

ORD-Eintrag
ord-cd82921d1e7842109441306466628c1d
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410530

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