Acetic Acid → (5-Benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid

HRID 358096

Reaction equation

HRID 358096 reaction equation
[C:1]([CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[S:11])([OH:3])=[O:2].C([O-])(=O)C.[Na+].C(O)(=O)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[C:1]([CH2:4][N:5]1[C:9](=[O:10])[C:8](=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:7][C:6]1=[S:11])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 517045Sodium Acetate

Product 1

HCID 2769989(5-Benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acidYield 50.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 955 mg of 3-carboxymethylrhodanine, 516 mg of sodium acetate, 10 ml of acetic acid and 637 mg of benzaldehyde was heat-refluxed for 2 hours. To the reaction mixture was added 20 ml of water, and the precipitated crystals were filtered. The resulting crystals were recrystallized from ethanol to obtain 699 mg of the titled compound.

Workup

  1. temperaturewas heat-refluxed for 2 hours
  2. filtrationthe precipitated crystals were filtered
  3. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-a75a90f5f67d4c06882b1814f400cfc3
Source dataset
uspto-grants-1984_08
Patent number
US04464382

Linked notes

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