Reaktion #215925

ord-f0a802d59c9c4788a1516338c94a138d

Reaktionsgleichung

COc1cc(C=O)ccc1O
4-hydroxy-3-methoxybenzaldehyde
CN1CC(=O)NC1=O
1-methyl hydantoin
NCCC(=O)O
β-alanine
CC(=O)O
acetic acid
COc1cc(C=C2C(=O)NC(=O)N2C)ccc1O
product
Ausbeute 14.8%
COc1cc(C=C2C(=O)NC(=O)N2C)ccc1O
5- [(4-Hydroxy-3-methoxyphenyl )methylene ]-1-methyl-2,4imidazolidinedione
Ausbeute 14.8%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

A mixture of 4-hydroxy-3-methoxybenzaldehyde (4.6 g, 30 mmoles), 1-methyl hydantoin (3.5 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 8 hours the mixture is stirred into water (300 ml) and the precipitate filtered off, rinsed successively with water (3X), ethanol (2X), and ether (2X), and dried. Recrystallization from acetonitrile gave the pure product (1.1 g), mp 197°-198° C.

Quelle

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