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

HRID 247877Notes

Reaction equation

HRID 247877 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:11][N:12]1[C:16](=[O:17])[CH2:15][NH:14][C:13]1=[O:18].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[C:15]1[NH:14][C:13](=[O:18])[N:12]([CH3:11])[C:16]1=[O:17]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 86582-MethoxybenzaldehydeHCID 1388512,4-Imidazolidinedione, 3-methyl-HCID 517045Sodium Acetate

Product 1

HCID 541770415-[(2-Methoxyphenyl)methylene]-3-methyl-2,4-imidazolidinedioneYield 63.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-methoxybenzaldehyde (3.4 g,25 mmoles), 3-methyl hydantoin (3.0 g, 21 mmoles), sodium acetate (6.0 g, 73 mmoles), acetic anhydride (3 ml), and acetic acid (20 ml) is stirred under an inert atmosphere and heated to reflux. After 15 hours the mixture is poured into water (200 ml), stirred, and the precipitate filtered off, rinsed three times with water and dried. Recrystallization from acetonitrile gave the pure product (3.1 g), mp 189°-190° C.

Workup

  1. temperatureheated to reflux
  2. stirringstirred
  3. filtrationthe precipitate filtered off
  4. washrinsed three times with water
  5. customdried
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-d4fcc92c23f14244a83c75c92919786a
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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