Thiazolidinedione → 5-[1-(5-Benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methylidene]thiazolidine-2,4-dione

HRID 1811451Notes

Reaction equation

HRID 1811451 reaction equation
[CH2:1]([N:8]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[CH:13]=[C:12]([CH:23]=O)[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31]>C1(C)C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[CH2:1]([N:8]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[CH:13]=[C:12]([CH:23]=[C:29]3[S:25][C:26](=[O:31])[NH:27][C:28]3=[O:30])[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 5437ThiazolidinedioneHCID 862337835-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carboxaldehyde

Product 1

HCID 866139515-[1-(5-Benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methylidene]thiazolidine-2,4-dioneYield 80%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

592 mg of 5-benzyl-6-oxo-5,6-dihydrophenanthridine-2-carboxaldehyde and 221 mg of 2,4-thiazolidinedione were suspended in 10 ml of toluene. Two drops of acetic acid and two drops of piperidine were added to the suspension, followed by heating and refluxing overnight. The reaction liquid was cooled, and the solid thus obtained was collected by filtration. The collected solid was washed with toluene-diethyl ether, and dried, giving 620 mg (80% yield) of 5-[1-(5-benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methylidene]thiazolidine-2,4-dione as a yellow solid.

Workup

  1. temperatureby heating
  2. temperaturerefluxing overnight
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. customthe solid thus obtained
  6. filtrationwas collected by filtration
  7. washThe collected solid was washed with toluene-diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-2ff79f5966624f9b85db1e529c9f5692
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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