Reaktion #215917

ord-1b54489de7de41f3a8ce65b641fabe5d

Reaktionsgleichung

COc1cc(C=O)ccc1O
4-hydroxy-3-methoxybenzaldehyde
O=C1CNC(=O)N1
hydantoin
NCCC(=O)O
β-alanine
CC(=O)O
acetic acid
COc1cc(C=C2NC(=O)NC2=O)ccc1O
product
Ausbeute 42.7%
COc1cc(C=C2NC(=O)NC2=O)ccc1O
5- [(4-Hydroxy-3-methoxyphenyl )methylene ]-2,4-imidazolidinedione
Ausbeute 42.7%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturheated to reflux
  2. 2
    Filtrationthe precipitate is filtered off
  3. 3
    Waschenrinsed successively with water (3X), ethanol (2X), and ether (2X)
  4. 4
    Sonstigedried
  5. 5
    SonstigeRecrystallization from methanol

Vorschrift

A mixture of 4-hydroxy-3-methoxybenzaldehyde (4.6 g, 30 mmoles), hydantoin (3.0 g, 30 mmoles), β-alanine (1.4 g, 16 mmoles), and acetic acid (40 ml) is stirred under an inert atmosphere and heated to reflux. After 4 hours the mixture is stirred into water (350 ml) and the precipitate is filtered off, rinsed successively with water (3X), ethanol (2X), and ether (2X), and dried. Recrystallization from methanol afforded the pure product (3.0 g), mp 272°-273° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05464856uspto-grants-1995_11