N,N'-Dimethylethylenediamine → Ethyl p-(2-oxo-1,3-oxazolidin-3-yl)benzoate

HRID 1803943

Reaktionsgleichung

Reaktionsgleichung von HRID 1803943
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[O:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[O:18]=[C:14]1[N:15]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16][CH2:17][O:13]1

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 142891Ethyl 4-iodobenzoate

Produkt 1

HCID 616604Ethyl p-(2-oxo-1,3-oxazolidin-3-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 4-iodobenzoate (1.5 mL), oxazolidin-2-one (940 mg), potassium carbonate (2.5 g) and copper (I) iodide (171 mg) were added toluene (9 mL) and N,N′-dimethylethylenediamine (195 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform) to give the title compound (1.2 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-9fc62e2fb21f470c88216cdd48a9e957
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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