Hydrochloric Acid → 4-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 401074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401074
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:26][CH2:27][CH3:28])[C:24]=1[OH:25])[CH:20]=O.[NH2:29][C:30]([NH2:32])=[O:31].Cl>CCO>[Br:16][C:17]1[CH:18]=[C:19]([CH:20]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:22]=[C:23]([O:26][CH2:27][CH3:28])[C:24]=1[OH:25]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Produkt 1

HCID 569614644-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-oneAusbeute 11,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1,2-diphenylethanone (4.80 g, 25 mmol), 3-bromo-5-ethoxy-4-hydroxybenzaldehyde (5.00 g, 20 mmol) and urea (3.68 g, 61 mmol) in EtOH (250 mL) was added conc. HCl (10 mL). The mixture was heated at reflux for 112 h. Followed standard aqueous workup procedure and purified by silica gel column chromatography (PE:EA=1:3) to afford Compound 100 as a white solid (1.06 g, 11%). 1H NMR (MeOH-d4 500 MHz TMS): δ 7.24 (s, 5H), 7.09 (s, 1H), 7.04 (s, 3H), 6.85 (s, 3H), 5.17 (s, 1H), 4.03 (m, 2H), 1.37 (t, J=7.5 Hz, 3H); MS (ESI): m/z 465.0 [M+1]+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 112 h
  3. customFollowed standard aqueous workup procedure and purified by silica gel column chromatography (PE:EA=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-0dd0b390d26145bd955ace1a122554ad
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741915B2

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