Piperidine → 3-Amino-5-(4-phenoxybenzylidene)-2-thioxothiazolidin-4-one

HRID 2172831Notes

Reaction equation

HRID 2172831 reaction equation
[NH2:1][N:2]1[C:6](=[O:7])[CH2:5][S:4][C:3]1=[S:8].[O:9]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CCCCC1>C(O)C>[NH2:1][N:2]1[C:6](=[O:7])[C:5](=[CH:20][C:19]2[CH:22]=[CH:23][C:16]([O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:17][CH:18]=2)[S:4][C:3]1=[S:8]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 661394-PhenoxybenzaldehydeHCID 740333-Aminorhodanine

Product 1

HCID 5016253-Amino-5-(4-phenoxybenzylidene)-2-thioxothiazolidin-4-oneYield 68.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-aminorhodanine (1.00 g) in ethanol (20 ml) were added 4-phenoxybenzaldehyde (1.47 g) and piperidine (57 mg), and the mixture was heated with reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform) to give 3-amino-5-(4-phenoxybenzylidene)-2-thioxothiazolidin-4-one (1.52 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-b798e8f2431342299a4913356416de04
Source dataset
uspto-grants-2015_06
Patent number
US09056862B2

Reaction notes

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