Thiazolidinedione → HCID 20703757, compound

HRID 1461248Notes

Reaction equation

HRID 1461248 reaction equation
S1CC(=O)NC1=O.OCCOC1C=CC(C=O)=CC=1.N1CCCCC1.[OH:26][CH2:27][CH2:28][O:29][C:30]1[CH:43]=[CH:42][C:33]([CH:34]=[C:35]2[S:39][C:38](=[O:40])[NH:37][C:36]2=[O:41])=[CH:32][CH:31]=1.[Mg]>C1(C)C=CC=CC=1.O.C(O)(=O)C>[OH:26][CH2:27][CH2:28][O:29][C:30]1[CH:43]=[CH:42][C:33]([CH2:34][CH:35]2[S:39][C:38](=[O:40])[NH:37][C:36]2=[O:41])=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-HCID 5462224MagnesiumHCID 53901783HCID 53901783, compound

Product 1

HCID 20703757HCID 20703757, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2,4-Thiazolidinedione (46g) and 4-(2-hydroxyethoxy)-benzaldehyde (65g) were mixed in toluene (400ml) containing acetic acid (1.0 ml) and piperidine (1.0 ml) in an apparatus incorporating a water-trap. The mixture was boiled under reflux with vigorous stirring for 30 minutes, during which time the theoretical quantity of water was obtained and 5-[4-(2-hydroxyethoxy)benzylidene]-2,4-thiazolidinedione started to crystallise. The solution was cooled and the benzylidene compound (mp 194° C.-196° C.) collected by filtration. This product was suspended in methanol (2 l.) and treated portionwise with magnesium turnings (2 g). When the vigorous reaction started a cooling bath was applied and the rest of the magnesium (78 g) was added portionwise with stirring. The mixture was stirred overnight at ambient temperature and the solvent was then evaporated. 5% Hydrochloric acid solution (1000 ml), water (500 ml) and methanol (500 ml) were added. When gas evolution ceased the mixture was extracted with dichloromethane, the organic phase dried (MgSO4), filtered and evaporated under reduced pressure. The title compound was obtained pure by crystallisation from aqueous methanol (m.p. 137°-9° C.).

Workup

  1. temperatureunder reflux
  2. customwas obtained
  3. customto crystallise
  4. temperatureThe solution was cooled
  5. filtrationthe benzylidene compound (mp 194° C.-196° C.) collected by filtration
  6. additiontreated portionwise with magnesium turnings (2 g)
  7. customWhen the vigorous reaction
  8. stirringThe mixture was stirred overnight at ambient temperature
  9. customthe solvent was then evaporated
  10. addition5% Hydrochloric acid solution (1000 ml), water (500 ml) and methanol (500 ml) were added
  11. extractionwas extracted with dichloromethane
  12. dry with materialthe organic phase dried (MgSO4)
  13. filtrationfiltered
  14. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d4d61952dc554930b44db8ccda2153e7
Source dataset
uspto-grants-1991_12
Patent number
US05075300

Reaction notes

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