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

HRID 247881Notes

Reaction equation

HRID 247881 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-f7f68f6dcb16413fa2f1049121f0ce53
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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