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

HRID 504042Notes

Reaction equation

HRID 504042 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-da9478555b334f33a39badf8b30fa6cf
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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