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

HRID 1464648Notes

Reaction equation

HRID 1464648 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 l), 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-ae991b3d39bf440793e8a25a8fb79989
Source dataset
uspto-grants-1994_04
Patent number
US05306822

Reaction notes

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