Beta-Alanine → HCID 53632063, Verbindung

HRID 1885246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885246
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[S:25].NCCC(O)=O.O>C(O)(=O)C>[CH3:4][C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:23]2[N:19]([CH3:18])[C:20](=[S:25])[NH:21][C:22]2=[O:24])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 239Beta-AlanineHCID 962WaterHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 33414471-Methyl-2-sulfanylideneimidazolidin-4-one

Produkt 1

HCID 53632063HCID 53632063, VerbindungAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (19.0 g, 81 mmols), 1-methyl-2-thioxo-4-imidazolidinone (10.6 g, 81 mmols) and beta-alanine (4.7 g, 53 mmols) in acetic acid (150 ml) is stirred under an inert atmosphere and heated to reflux. After 5 hours the mixture is allowed to cool, and is stirred into water (1.5 L). After an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (17.5 g), mp 242°-244° C.

Aufarbeitung

  1. temperatureheated to reflux
  2. temperatureto cool
  3. filtrationAfter an hour the product is filtered off
  4. washwashed three times with water
  5. customdried
  6. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-81e6b6da63d64ec586dfb097c7af7be4
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143928

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