Ethanol → HCID 54151686, compound

HRID 2394391Notes

Reaction equation

HRID 2394391 reaction equation
C(O)C.[CH2:4]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=O)[C:14]=2[CH:13]=[CH:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1CCCCC1.[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34]>C(OCC)C>[CH2:4]([N:11]1[C:19]2[C:14](=[C:15]([CH:20]=[C:32]3[S:28][C:29](=[O:34])[NH:30][C:31]3=[O:33])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 17221112HCID 17221112, compound

Product 1

HCID 54151686HCID 54151686, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To 60 ml of ethanol, there were dissolved 3.00 g of 1-benzylindole-4-carbaldehyde prepared in Example 1 and 0.22 g of piperidine, followed by addition of 2.99 g of 2,4-thiazolidinedione to the resulting solution and heating the mixture under reflux for 24 hours. To the reaction solution, there was added 120 ml of diethyl ether and the mixture was stirred at 0° C. for one hour. The crystals precipitated were filtered off and washed with a diethyl ether/ethanol (2:1) mixed solvent. The crystals were dried under reduced pressure to give 3.24 g of 5-(1-benzylindol-4-yl)methylene-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 76%.

Workup

  1. temperatureheating the mixture
  2. temperatureunder reflux for 24 hours
  3. customThe crystals precipitated
  4. filtrationwere filtered off
  5. washwashed with a diethyl ether/ethanol (2:1)
  6. additionmixed solvent
  7. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-c4b5f6acd22849d1bbcfc630c8ccd160
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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