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Potassium Carbonate → 2-[1-Methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazole

HRID 1534379
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1534379
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:19][C:20]1[C:21](=[O:31])[N:22]([CH3:30])[C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:12][O:11][C:8]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:19][C:20]2[C:21](=[O:31])[N:22]([CH3:30])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:3]=1)[CH2:9][CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenolHCID 200819733-(Bromomethyl)-1-methyl-2(1H)-quinolinone

Produkt 1

HCID 191016402-[1-Methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.5 g, 2 mmol), 3-bromomethyl-1,2-dihydro-1-methylquinolin-2-one (0.5 g, 2 mmol), potassium carbonate (0.35 g, 2.5 mmol) and dimethylformamide (3 ml) was stirred at ambient temperature for 48 hours. The mixture was filtered, the filtrate was added to water (30 ml) and the mixture was extracted with elhyl acetate (3×15 ml). The organic extracts were combined, washed with a dilute aqueous sodium hydroxide solution and with a saturated sodium chloride solution dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with toluene/ethyl acetate (7/3 v/v) to give 2-[1-methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazole (0.84 g, 100%), m.p. 123°-125° C.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was added to water (30 ml)
  3. extractionthe mixture was extracted with elhyl acetate (3×15 ml)
  4. washwashed with a dilute aqueous sodium hydroxide solution and with a saturated sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with toluene/ethyl acetate (7/3 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-5e79772ceb3c4e4f9b7f073c81aa73b2
Quelldatensatz
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05089495

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