Acetic Acid → HCID 86625167, compound

HRID 2375545Notes

Reaction equation

HRID 2375545 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].C(O)(=O)C.N1CCCCC1.[Cl:18][CH:19]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][N:31]=1)[CH2:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Cl:18][CH:19]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][N:31]=1)[CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH:26]=[C:5]2[S:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 713792474-[2-Chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde

Product 1

HCID 86625167HCID 86625167, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2 g (0.017 mol) thiazolidin-2,4-dione, 2 g (0.034 mol) acetic acid and 3 g (0.03 mol) piperidine were added to a solution of 5 g (0.017 mol) 4-[2-chloro-2-(5-ethyl-pyridin-2-yl)-ethoxy]-benzaldehyde dissolved in 50 mL toluene. Reaction mixture was heated and water was removed azeotropically. After completion of the reaction on TLC, toluene was distilled out completely under reduced pressure. Product was poured into excess of water and extracted with ethyl acetate. After concentrating ethyl acetate in vacuo and making its HCl salt in usual way 4.3 g (60%) desired product obtained.

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. customwater was removed azeotropically
  4. customAfter completion of the reaction on TLC, toluene
  5. distillationwas distilled out completely under reduced pressure
  6. additionProduct was poured into excess of water
  7. extractionextracted with ethyl acetate
  8. concentrationAfter concentrating ethyl acetate in vacuo
  9. customobtained

Sources & evidence

ORD record
ord-f446b517c2a949a99917262b1ba22ac6
Source dataset
uspto-grants-2008_12
Patent number
US07465801B2

Reaction notes

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