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N,N'-Dimethylethylenediamine → Ethyl 4-(5-methoxymethyl-2-oxooxazolin-3-yl)benzoate

HRID 1803974
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1803974
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[NH:6][CH2:5]1.I[C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[O:8][C:7](=[O:9])[N:6]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 103131495-(Methoxymethyl)oxazolidin-2-one

Produkt 1

HCID 67380766Ethyl 4-(5-methoxymethyl-2-oxooxazolin-3-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

By reaction and treatment in the same manner as in Preparation Example 25 and using 1-amino-3-methoxypropan-2-ol (1 g), 5-methoxymethyloxazolidin-2-one (620 mg) was obtained. To a mixture of 5-methoxymethyloxazolidin-2-one (620 mg), ethyl 4-iodobenzoate (1.6 mL), potassium carbonate (2.6 g) and copper (I) iodide (552 mg) were added toluene (20 mL) and N,N′-dimethylethylenediamine (625 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 to give the title compound (830 mg).

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

Quellen und Nachweise

ORD-Eintrag
ord-6474c16a1aa34b2085516384c64e2fbd
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354401B2

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