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Potassium Carbonate → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-one

HRID 554975
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 554975
[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])=[N:6][C:5]=1[CH3:15])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH:22]1([CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:24][CH2:23]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:26][CH2:25][CH:22]3[CH2:24][CH2:23]3)[C:10]2=[O:14])=[N:6][C:5]=1[CH3:15])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterHCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

Produkt 1

HCID 666615211-(5-Acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-oneAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one (4.50 g, 20.00 mmol), tetrabutylammonium iodide (0.10 g) and potassium carbonate (4.00 g, 28.92 mmol) in 1,4-dioxane (100 mL) was added 2-cyclopropylethyl-4-methylbenzenesulfonate (6.00 g, 24.96 mmol). The reaction mixture was heated to reflux for 37 h. The solvent was removed in vacuo. The residue was dissolved in water (50 mL) and extracted with ethyl acetate. The organic solution washed with water and brine and dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography to afford 1-(5-acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-one in 37% yield (2.20 g): mp 82-83° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 4.12-4.06 (m, 2H), 3.63-3.57 (m, 2H), 3.40 (t, J=7.2 Hz, 2H), 2.60 (s, 3H), 2.44 (s, 3H), 1.51-1.44 (m, 2H), 0.71-0.62 (m, 1H), 0.49-0.43 (m, 2H), 0.09-0.04 (m, 2H); MS (ES+) m/z 294.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 37 h
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in water (50 mL)
  5. extractionextracted with ethyl acetate
  6. washThe organic solution washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3eb151d0371241bdb6bdb320d0c1d826
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08049016B2

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