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

HRID 247864

Reaction equation

HRID 247864 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]

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 962WaterSolvent

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 (3×), ethanol (2×), and ether (2×), 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 (3×), ethanol (2×), and ether (2×)
  4. customdried

Sources & evidence

ORD record
ord-2062fc42fbed44ee80bba714c5724e0e
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Linked notes

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