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Acetic Acid → 4-Thiazolidinone, 5-[(2,3-dimethoxyphenyl)methylene]-2-thioxo-

HRID 128726
Notes
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Reaction equation

HRID 128726 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[S:13]1[CH2:19][C:17](=[O:18])[NH:16][C:14]1=[S:15].C([O-])(=O)C.[Na+].C(O)(=O)C>O>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[C:19]1[S:13][C:14](=[S:15])[NH:16][C:17]1=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 665812,3-DimethoxybenzaldehydeHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 46021174-Thiazolidinone, 5-[(2,3-dimethoxyphenyl)methylene]-2-thioxo-Yield 95.6%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 2,3-dimethoxybenzaldehyde (5.2 g, 30 mmoles), rhodanine (4.0 g, 29 mmoles), sodium acetate (8.4 g, 102 mmoles), and acetic acid (50 ml) is stirred under an inert atmosphere and heated to reflux. After 4 hours the mixture is stirred into water (250 ml) and the precipitate is filtered off, rinsed successively with water (3X), ethanol (2X), and ether (2X), and dried to afford the pure product (7.8 g), mp 268°-269° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed successively with water (3X), ethanol (2X), and ether (2X)
  4. customdried

Sources & evidence

ORD record
ord-2a1b9a28b05d49ec9b038ce22124b7f3
Source dataset
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05464856

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes