Benzoic Acid → HCID 73504064, compound

HRID 2260704Notes

Reaction equation

HRID 2260704 reaction equation
[C:1]1([CH:7]2[S:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19](C=O)=[CH:18][CH:17]=3)[C:8]2=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCC[CH2:33]1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([CH:7]2[S:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:33]=[C:29]4[S:25][C:26](=[O:31])[NH:27][C:28]4=[O:30])=[CH:18][CH:17]=3)[C:8]2=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 85657638HCID 85657638, compound

Product 1

HCID 73504064HCID 73504064, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[2-(5-phenyl-2,4-thiazolidinedion-3-yl) ethoxy]-benzaldehyde) (1.5 g) 2,4-thiazolidinedione (0.54 g), piperidine (0.4 ml) and benzoic acid (0.2 g) was heated at reflux in toluene (100 ml) in a Dean and Stark apparatus. After 4 hours at reflux the mixture was allowed to cool to room temperature overnight and then evaporated to dryness. The residue was then triturated with diisopropyl ether for 24 hours. The resulting solid was filtered off, washed with ether and dried in vacuo to afford the title compound which softened at 80° C. and melted at 120° C.

Workup

  1. temperaturewas heated
  2. temperatureAfter 4 hours at reflux the mixture
  3. customevaporated to dryness
  4. customThe residue was then triturated with diisopropyl ether for 24 hours
  5. filtrationThe resulting solid was filtered off
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-671a4d7db8d94206b30496fbf5ee1dbb
Source dataset
uspto-grants-1995_12
Patent number
US05478850

Reaction notes

Loading…