Acetic Acid → HCID 54385620, compound

HRID 128743

Reaction equation

HRID 128743 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].[CH3:12][N:13]1[CH2:19][C:17](=[O:18])[NH:16][C:14]1=[O:15].NCCC(O)=O.C(O)(=O)C>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:19]2[N:13]([CH3:12])[C:14](=[O:15])[NH:16][C:17]2=[O:18])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 1183VanillinHCID 692171-Methylhydantoin

Product 1

HCID 54385620HCID 54385620, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate filtered off
  3. washrinsed successively with water (3X), ethanol (2X), and ether (2X)
  4. customdried
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-f0a802d59c9c4788a1516338c94a138d
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Linked notes

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