Water → 5-((4-Phenylthiophen-2-yl)methylene)-2-thioxothiazolidin-4-one

HRID 1397213Notes

Reaction equation

HRID 1397213 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:14]1[CH2:20][C:18](=[O:19])[NH:17][C:15]1=[S:16].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[C:20]3[S:14][C:15](=[S:16])[NH:17][C:18]3=[O:19])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 1201546RhodanineHCID 50094674-Phenylthiophene-2-carbaldehyde

Product 1

HCID 472983595-((4-Phenylthiophen-2-yl)methylene)-2-thioxothiazolidin-4-oneYield 87.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-phenyl thiophene-2-carboxaldehyde (1 g, 5.3 mmol) and rhodanine (700 mg, 5.3 mmol) in 10 mL of glacial acetic acid was heated with anhydrous sodium acetate (1.22 g, 14.8 mmol) for 2 h. The reaction mixture was then poured into cold water. The precipitate was filtered, washed with water and dried under reduced pressure to get 5-((4-phenylthiophen-2-yl)methylene)-2-thioxothiazolidin-4-one (1.4 g, yield 87%). MS (ESI) m/z: Calculated for C14H9NOS3: 302.98. found: 302.0 (M−H)−. The crude product was carried through without further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-8994e429df374039a6c57efdd9a10123
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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