Acetic Anhydride → 5-[(2-Methoxyphenyl)methylene]-2-thioxo-4-imidazolidinone

HRID 128734

Reaction equation

HRID 128734 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[NH:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[S:13].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:17]1[NH:11][C:12](=[S:13])[NH:14][C:15]1=[O:16]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 86582-MethoxybenzaldehydeHCID 517045Sodium AcetateHCID 12740302-Thiohydantoin

Product 1

HCID 30046725-[(2-Methoxyphenyl)methylene]-2-thioxo-4-imidazolidinoneYield 85.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-methoxybenzaldehyde (2.5 g, 18 mmoles), 2-thiohydantoin (2.0 g, 17 mmoles), sodium acetate (4.0 g, 49 mmoles), acetic anhydride (μml), and acetic acid (15 ml) is stirred under an inert atmosphere and heated to reflux. After 1 hour the mixture is stirred into water (300 ml), and the precipitate is filtered off, rinsed with water three times and dried. The product is triturated in boiling methanol, filtered off, and dried to afford the pure product (3.4 g), mp 234°-235° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed with water three times
  4. customdried
  5. customThe product is triturated
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-c994d1b65e984355a391b6af2b305182
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Linked notes

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