Benzoic Acid → 5-(4-(2-Chlorophenyl)benzylidene)thiazolidine-2,4-dione

HRID 1394159

Reaction equation

HRID 1394159 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[CH:5][CH:4]=1)=O.[S:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1.O>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[C:20]2[S:16][C:17](=[O:22])[NH:18][C:19]2=[O:21])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 13944002'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 723570485-(4-(2-Chlorophenyl)benzylidene)thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-formyl-(2′-chloro-1,1′-biphenyl) (0.12 g, 0.55 mmol) and 2,4-thiazolidinedione (0.08 g, 0.65 mmol) in toluene (10 mL) were added piperidine (0.008 mL, 0.073 mMol) and benzoic acid (0.011 mg, 0.08 mmol), and the reaction was refluxed for 4 h with continuous removal of water. The solvent was then distilled off and the oily residue obtained was purified by chromatography on silica-gel using hexane: ethyl acetate (3:1) as the eluent to yield titled product.

Workup

  1. distillationThe solvent was then distilled off
  2. customthe oily residue obtained
  3. customwas purified by chromatography on silica-gel

Sources & evidence

ORD record
ord-358e086a5c514b15b5aa7514def9cb2f
Source dataset
uspto-grants-2008_03
Patent number
US07348348B2

Linked notes

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