Acetic Acid → HCID 75180723, compound

HRID 475519Notes

Reaction equation

HRID 475519 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[S:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[C:20]2[S:16][C:17](=[O:22])[NH:18][C:19]2=[O:21])=[CH:10][CH:9]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21703917HCID 21703917, compound

Product 1

HCID 75180723HCID 75180723, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-(2-isopropoxyethoxy)benzaldehyde obtained in step (0.98 g, 4.71 mmol) and 2,4-thiazolidinedione (0.55 g, 4.71 mmol) were dissolved in 20 ml of toluene, piperidine (0.23 ml, 2.36 mmol) and acetic acid (0.13 ml, 2.36 mmol) were subsequently added thereto, and the resulting solution was heated overnight under reflux in a Dean-Stark water trap. Then, the mixture thus obtained was cooled and filtered. The precipitate was washed with ether or hexane and dried to afford Derivative 1 having the above formula, (5-(4-(2-isopropoxyethoxy)benzylidene)thiazolidine-2,4-dione) (1.26 g, yield: 87.5%) as yellow solid.

Workup

  1. temperaturethe resulting solution was heated overnight
  2. customThen, the mixture thus obtained
  3. temperaturewas cooled
  4. filtrationfiltered
  5. washThe precipitate was washed with ether or hexane
  6. customdried

Sources & evidence

ORD record
ord-c079387803a3477181f1b0ae8bdd9034
Source dataset
uspto-grants-2014_01
Patent number
US08637558B2

Reaction notes

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