Sodium Acetate → 3-(2,4-Dimethyl-phenyl)-5-[5-(3-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one

HRID 409938

Reaction equation

HRID 409938 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][S:11][C:10]1=[S:15].C([O-])(=O)C.[Na+].[N+:21]([C:24]1[CH:25]=[C:26]([C:30]2[O:34][C:33]([CH:35]=O)=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12](=[CH:35][C:33]2[O:34][C:30]([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=3)=[CH:31][CH:32]=2)[S:11][C:10]1=[S:15]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 6124175-(3-Nitrophenyl)furfuralHCID 19078563-(2,4-Dimethyl-phenyl)-2-thioxo-thiazolidin-4-one

Product 1

HCID 761915313-(2,4-Dimethyl-phenyl)-5-[5-(3-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 4.7 mL of 0.2 M ethanol was dissolved 0.1 g of 3-(2,4-dimethyl-phenyl)-2-thioxo-thiazolidin-4-one (0.42 mmol) synthesized in 1. The solution was mixed with 0.11 g of sodium acetate (1.34 mmol) and 0.15 g of 5-(3-nitro-phenyl)-furan-2-carboaldehyde (0.69 mmol), synthesized in 2, with stirring, and then heated for 4 hrs. The resulting reaction mixture was washed with ethanol to afford the title compound as a solid. When a solid was not formed, purification by silica gel column chromatography afforded 0.54 g of the title compound (yield: 28.6%).

Workup

  1. customsynthesized in 1
  2. customsynthesized in 2
  3. temperatureheated for 4 hrs
  4. customThe resulting reaction mixture
  5. washwas washed with ethanol

Sources & evidence

ORD record
ord-e56b6a68ef964a2199bb807c73aa1a10
Source dataset
uspto-grants-2014_06
Patent number
US08759536B2

Linked notes

Loading…