Acetic Acid → HCID 21704996, compound

HRID 1595509Notes

Reaction equation

HRID 1595509 reaction equation
[CH3:1][NH:2][C:3](=[O:28])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1.C(O)(=O)C>CN(C)C=O.[Pd]>[CH3:1][NH:2][C:3](=[O:28])[NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:15]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86757375HCID 86757375, compound

Product 1

HCID 21704996HCID 21704996, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

1.2 g (3.02 mmole) 5-(4-[2-(4-methylureidophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione was hydrogenated for 18 hours in 100 ml dimethylformamide and 10 ml acetic acid with 1 g Pd/C (10%) as catalyst. The catalyst was filtered off and the solvent was evaporated in vacuo. Ethyl acetate was added and the product was extracted with potassium carbonate in water. A black precipitate was filtered off and the ethyl acetate phase was extracted with more potassium carbonate solution. The water phase was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and evaporated in vacuo and recrystallized in methanol to give 0.71 g (yield 59%) of the desired product.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated in vacuo
  3. additionEthyl acetate was added
  4. extractionthe product was extracted with potassium carbonate in water
  5. filtrationA black precipitate was filtered off
  6. extractionthe ethyl acetate phase was extracted with more potassium carbonate solution
  7. extractionextracted with ethyl acetate
  8. customThe organic phase was dried
  9. customevaporated in vacuo
  10. customrecrystallized in methanol

Sources & evidence

ORD record
ord-6a614566148b42de88dee8f0b829e3bf
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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