Acetic Anhydride → 5-[(3-Methoxyphenyl)methylene]-1-methyl-2,4-imidazolidinedione

HRID 1464652Notes

Reaction equation

HRID 1464652 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1C=O.[CH3:11][N:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[O:14].[C:19]([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:7]([CH:19]=[C:18]2[N:12]([CH3:11])[C:13](=[O:14])[NH:15][C:16]2=[O:17])[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 86582-MethoxybenzaldehydeHCID 692171-MethylhydantoinHCID 517045Sodium Acetate

Product 1

HCID 544632705-[(3-Methoxyphenyl)methylene]-1-methyl-2,4-imidazolidinedioneYield 18.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-methoxybenzaldehyde (3.8 g, 28 mmoles), 1-methyl hydantoin (3.0 g 26 mmoles), sodium acetate (8.4 g, 102 mmoles), acetic anhydride (10 ml), and acetic acid (40 ml) is stirred under an inert atmosphere and heated to reflux. After 24 hours the mixture is stirred into water (350 ml), stirred, and the resulting gum is isolated and washed by decantation, then crystallized from isopropanol. Recrystallization from acetonitrile gave the pure product (1.1 g), mp 195°-197° C.

Workup

  1. temperatureheated to reflux
  2. stirringstirred
  3. customthe resulting gum is isolated
  4. washwashed by decantation
  5. customcrystallized from isopropanol
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-28488c3db274414cb4e8a34e51cef960
Source dataset
uspto-grants-1994_04
Patent number
US05306822

Reaction notes

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