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

HRID 128738Notes

Reaction equation

HRID 128738 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-bc56d6805cce4995b3c7d986cd6874f3
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Reaction notes

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