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Urea → ({3-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid

HRID 422063
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 422063
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[O:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:4][C:3]=1[CH3:23].[NH2:24][C:25]([NH2:27])=[O:26]>Cl.O1CCOCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])[CH:19]=[CH:20][CH:21]=3)[NH:24][C:25](=[O:26])[N:27]=2)=[CH:4][C:3]=1[CH3:23]
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Komponenten

5

Edukt 2

HCID 1176UreaHCID 57831167(E)-2-(3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acid

Produkt 1

HCID 178422597({3-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acidAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

(E)-2-(3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acid (15.0 g, 48.0 mmol) and urea (14.4 g, 0.24 mol) were suspended in 200 mL of 4N HCl solution in dioxane, and the reaction mixture was heated to reflux overnight, then cooled to room temperature. The resulted mixture was concentrated in vacuo to remove dioxane. The residues were suspended in 150 mL of 2-propanol and heated in a 90° C. oil bath for 10 minutes, then cooled down to room temperature. The suspension was filtered and washed with 50 mL of 2-propanol and dried in the air. 9.2 g (54%) of the desired ({3-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid were obtained. 1H NMR (400 MHz, DMSO-d6): 10.39 (s, 1H), 8.00 (s, 1H), 7.90 (m, 1H), 7.75 (m, 1H), 7.65 (s, 1H), 7.40-7.55 (m, 2H), 7.16 (m, 1H), 6.95 (m, 1H), 4.80 (s, 2H), 2.20 (s, 3H). MS (EI) for C19H16N2O5: 353 (MH+).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe resulted mixture was concentrated in vacuo
  4. customto remove dioxane
  5. temperatureheated in a 90° C. oil bath for 10 minutes
  6. temperaturecooled down to room temperature
  7. filtrationThe suspension was filtered
  8. washwashed with 50 mL of 2-propanol
  9. customdried in the air

Quellen und Nachweise

ORD-Eintrag
ord-eb0f057416c34720997a05c0194e2872
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08101625B2

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