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Hydrochloric Acid → 5-Methoxycarbonyl-4-(2-ethoxy-6-pentadecylphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

HRID 424859
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 424859
[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5]([CH3:7])=O.[CH2:9]([O:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:13]=1[CH:14]=O)[CH3:10].[NH2:35][C:36]([NH2:38])=[O:37].Cl>O1CCCC1>[CH3:1][O:2][C:3]([C:4]1[CH:14]([C:13]2[C:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:17][CH:18]=[CH:19][C:12]=2[O:11][CH2:9][CH3:10])[NH:35][C:36](=[O:37])[NH:38][C:5]=1[CH3:7])=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 7757Methyl acetoacetateHCID 225745702-Ethoxy-6-pentadecyl benzaldehyde

Produkt 1

HCID 103687105-Methoxycarbonyl-4-(2-ethoxy-6-pentadecylphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of methylacetoacetate (1.2 g, 8.5 mmol), 2-ethoxy-6-pentadecyl benzaldehyde (3 g, 8.5 mmol) and urea (1.00 g, 17 mmol) in tetrahydrofuran (20 mL) was heated to reflux (65-70° C.) in the presence of hydrochloric acid (30%) for 7 h. The reaction mixture after being cooled to room temperature was poured into crushed ice (20 g) and stirred for 5 min. The viscous liquid was extracted with ethylacetate (40 mL) and was washed with 1N hydrochloric acid, water, sodium bicarbonate and brine. After drying over anhydrous sodium sulfate, the solvent was evaporated to yield light yellow oil. This crude product was purified by flash column chromatography and recrystallized from hexane to get white crystalline solid of title compound.

Aufarbeitung

  1. additionwas poured
  2. extractionThe viscous liquid was extracted with ethylacetate (40 mL)
  3. washwas washed with 1N hydrochloric acid, water, sodium bicarbonate and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customto yield light yellow oil
  7. customThis crude product was purified by flash column chromatography
  8. customrecrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-44a2ff48cc9145b0b73c541a9abdcbbe
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106062B1

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