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Methyl Ethyl Ketone → HCID 13532883, Verbindung

HRID 653002
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 653002
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH3:13])[N:6]=[CH:5]2.Br[CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:15]=1)[CH3:13])[N:6]=[CH:5]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 20195211HCID 20195211, Verbindung

Produkt 1

HCID 13532883HCID 13532883, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

A mixture of 4-[N-(6-chloro-2-quinazolinyl)-N-methylamino]phenol (0.52 g), ethyl 2-bromopropionate (0.40 g), potassium carbonate (0.28 g) and methyl ethyl ketone (25 ml) was heated under reflux for a period of 18 hours. After cooling, the mixture was diluted with water and the aqueous mixture was extracted with dichloromethane. The dichloromethane extract was dried (anhydrous sodium sulfate) and the solvent was removed under reduced pressure. The residue was purified by chromatography over silica gel (eluant dichloromethane) to give ethyl 2-{4-[N-(6-chloro-2-quinazolinyl)-N-methylamino]phenoxy}propionate as a yellow oil. The assigned structure was confirmed by proton magnetic resonance (pmr) spectroscopy and mass spectrometry. Pmr spectrum (CDCl3 ; δ in ppm): 8.93 (1H, s, quinazoline hetero ring proton); 7.60 (3H, s, quinazoline benzo-ring protons); 7.13 (4H, d of d, phenoxy protons); 4.80 (1H, q, CH--CH3); 4.27 (2H, q, CH2 --CH3); 1.60 (3H, d, CH--CH3); 1.27 (3H, t, CH2 --cH3).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 18 hours
  3. temperatureAfter cooling
  4. extractionthe aqueous mixture was extracted with dichloromethane
  5. extractionThe dichloromethane extract
  6. dry with materialwas dried (anhydrous sodium sulfate)
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by chromatography over silica gel (eluant dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-34742fd74a214b54b59c83d46b9c2a4f
Quelldatensatz
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04675047

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