Acetic Acid → HCID 86625168, compound

HRID 2094817Notes

Reaction equation

HRID 2094817 reaction equation
[Br:1][CH:2]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=1)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[S:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[Br:1][CH:2]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=1)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:25]2[S:21][C:22](=[O:27])[NH:23][C:24]2=[O:26])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 713792484-[2-Bromo-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde

Product 1

HCID 86625168HCID 86625168, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To stirred solution of 5 g (0.015 mol) 4-[2-bromo-2-(5-ethyl-pyridin-2-yl)-ethoxy]-benzaldehyde dissolved in 50 mL toluene was added 1.85 g (0.015 mol) thiazolidin-2,4-dione followed by addition of 2 g (0.03 mol) acetic acid and 3 g (0.03 mol) piperidine. 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. On concentrating ethyl acetate in vacuo, 0.65 g (10%) desired product obtained with satisfactory mass. The 1H NMR was similar to the 1H NMR of example 79.

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. concentrationOn concentrating ethyl acetate in vacuo, 0.65 g (10%) desired product
  9. customobtained with satisfactory mass

Sources & evidence

ORD record
ord-49095c771c1b4f7892805e0f523a6aa1
Source dataset
uspto-grants-2013_05
Patent number
US08445685B2

Reaction notes

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