Rhodanine → HCID 86613957, compound

HRID 504048Notes

Reaction equation

HRID 504048 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([CH:18]=O)[C:12]=3[CH2:11][CH2:10][C:9]2=[O:20])=[CH:3][CH:2]=1.[S:27]=[C:28]1[NH:32][C:31](=[O:33])[CH2:30][S:29]1>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:17]3[C:12](=[C:13]([CH:18]=[C:30]4[S:29][C:28](=[S:27])[NH:32][C:31]4=[O:33])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:20])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 1201546RhodanineHCID 86613958HCID 86613958, compound

Product 1

HCID 86613957HCID 86613957, compoundYield 116.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

1.50 g of 1-(biphenyl-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde and 0.761 g of 2-thioxo-1,3-thiazolidin-4-one were suspended in 20 ml of toluene. Two drops of piperidine and two drops of acetic acid were added to the suspension, followed by heating and refluxing for 4 hours. After allowing to cool, the solid thus precipitated was collected by filtration, and dried, giving 2.34 g (91% yield) of 1-(biphenyl-4-ylmethyl)-5-(4-oxo-2-thioxothiazolidine-5-ylidenemethyl)-3,4-dihydro-1H-quinolin-2-one as a yellow powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 4 hours
  3. temperatureto cool
  4. customthe solid thus precipitated
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-93b0589f70b047008b7d3e8e7fc5fe99
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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