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

HRID 2177955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177955
[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-42522f4553014ebe87fc3ae41d636d3a
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067893B2

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