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Acetic Acid → 3-n-Butyl-6-[4-(2-hydroxyethyl)aminophenyl]uracil

HRID 47970
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 47970
Cl[C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH2:11][CH3:12])[C:4](=[O:13])[CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18](CCO)=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C.[C:33](O)(=[O:35])[CH3:34]>O>[CH2:9]([N:5]1[C:4](=[O:13])[CH:3]=[C:2]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][CH2:34][CH2:33][OH:35])=[CH:20][CH:19]=2)[NH:7][C:6]1=[O:8])[CH2:10][CH2:11][CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 669044-Aminophenethyl alcoholHCID 81531DiisopropylethylamineHCID 141001713-butyl-6-chloropyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 226725173-n-Butyl-6-[4-(2-hydroxyethyl)aminophenyl]uracil

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-3-n-butyluracil (10.4 g, 51.3 mmol), 2-(4-aminophenyl)ethanol (10.0 g, 72.9 mmol) and ethyldiisopropylamine (18 ml, 0.1 mol) was heated with stirring under argon on a 150° oil bath for 1 hr 20 min. The mixture was cooled to room temperature, diluted with 50 ml of water, treated with 10 ml of acetic acid and stirred for crystallization overnight. A precipitated solid was filtered, washed with 2% acetic acid, dried on filter and dissolved in 100 ml of hot 96% ethanol. To the solution 100 ml of hot water was added followed by 1.0 g of charcoal. The mixture was filtered hot and crystallized on ice. Yellow solid was collected by filtration and dried in vacuum to yield 10.7 g of 40, mp 207-208° C. 1H NMR (DMSO-d6) δ0.88 (t, 3H, J=7.3 Hz, CH3), 1.25 (m, 2H, CH2), 1.46 (m, 2H, CH2), 2.70 (t, 2H, J=6.8 Hz, CH2), 3.60 (dd, 2H, J=11.8, 6.8 Hz, CH2), 3.68 (t, 2H, J=7.3 Hz, CH2), 4.62 (t, 1H, J=5.3 Hz, OH), 4.73 (d, 1H, J=1.8 Hz, 5-H), 7.10 (d, 2H, J=8.4 Hz, ArH), 7.23 (d, 2H, J=8.4 Hz, ArH), 7.10 (s, 1H, NH), 10.37 (s, 1H, NH).

Aufarbeitung

  1. temperaturewas heated
  2. stirringstirred for crystallization overnight
  3. filtrationA precipitated solid was filtered
  4. washwashed with 2% acetic acid
  5. customdried
  6. filtrationon filter
  7. dissolutiondissolved in 100 ml of hot 96% ethanol
  8. additionTo the solution 100 ml of hot water was added
  9. filtrationThe mixture was filtered hot
  10. customcrystallized on ice
  11. filtrationYellow solid was collected by filtration
  12. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1a7cd3c3748e4adba57b3e8f5969d752
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06699975B2

Notizen zur Reaktion

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