Thiazolidinedione → HCID 53877217, compound

HRID 619354Notes

Reaction equation

HRID 619354 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=O)=[CH:3][CH:2]=1.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].N1CCCCC1>C(O)C>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:2]=[CH:3][C:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[C:27]2[S:23][C:24](=[O:29])[NH:25][C:26]2=[O:28])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 15050018HCID 15050018, compound

Product 1

HCID 53877217HCID 53877217, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the above benzaldehyde (500 g, 17 mmol), 2,4-thiazolidinedione (3.03 g, 26 mmol) and piperidine (0.35 ml, 3.5 mmol) in ethanol (75 ml) was stirred at reflux temperature for 16 h. The reaction mixture was cooled and the precipitated was filtered off and washed thoroughly with ethanol and dried in vacuo at 50° C. The solid was first washed with a mixture of ethyl acetate, heptane and dichloromethane (1:1:6, 40 ml) and then washed with dichloromethane (20 ml). Drying in vacuo at 50° C. afforded 1.88 g (28%) of the title compound as a solid.

Workup

  1. temperatureat reflux temperature for 16 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe precipitated was filtered off
  4. washwashed thoroughly with ethanol
  5. customdried in vacuo at 50° C
  6. washThe solid was first washed with a mixture of ethyl acetate, heptane and dichloromethane (1:1:6, 40 ml)
  7. washwashed with dichloromethane (20 ml)
  8. customDrying in vacuo at 50° C.

Sources & evidence

ORD record
ord-1907f5e02ae548ee998baff0346c1f19
Source dataset
uspto-grants-1999_09
Patent number
US05958957

Reaction notes

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