Thiazolidinedione → HCID 53991118, compound

HRID 892816Notes

Reaction equation

HRID 892816 reaction equation
[C:1]1([CH2:7][CH2:8][S:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].C([O-])(=O)C.[Na+]>>[C:1]1([CH2:7][CH2:8][S:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[C:22]3[S:18][C:19](=[O:24])[NH:20][C:21]3=[O:23])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 5437ThiazolidinedioneHCID 517045Sodium AcetateHCID 14459966HCID 14459966, compound

Product 1

HCID 53991118HCID 53991118, compoundYield 11.8%

Procedure

4-(2-Phenylethylthio)benzaldehyde (12.4 mmol, 3.0 g), 2,4-thiazolidinedione (15.5 mmol, 1.81 g) and anhydrous sodium acetate (30.9 mmol, 2.54 g) were heated in an oil bath at 150° C. for 0.5 hour. The mixture was cooled and the resulting solid triturated with water (100 ml) and collected by filtration. The solid was recrystallized from methanol:ethyl acetate:acetone (1:1:2) to afford 500 mg of title product; m.p. 182°-183° C.

Workup

  1. temperatureThe mixture was cooled
  2. customthe resulting solid triturated with water (100 ml)
  3. filtrationcollected by filtration
  4. customThe solid was recrystallized from methanol:ethyl acetate:acetone (1:1:2)

Sources & evidence

ORD record
ord-98717233d6624e19923ae1490fea8188
Source dataset
uspto-grants-1992_06
Patent number
US05120754

Reaction notes

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