Acetic Acid → 5-[(4-Hydroxy-3-methoxyphenyl)methylene]-1-methyl-2,4-imidazolidinedione

HRID 247882Notes

Reaction equation

HRID 247882 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 543856205-[(4-Hydroxy-3-methoxyphenyl)methylene]-1-methyl-2,4-imidazolidinedioneYield 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 (3×), ethanol (2×), and ether (2×) 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 (3×), ethanol (2×), and ether (2×)
  4. customdried
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-9797643a1f9c4c158e8c3ff47b3e2490
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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