HCID 54012500, compound → HCID 21704995, compound

HRID 1595522Notes

Reaction equation

HRID 1595522 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH:19]=[C:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 1

HCID 54012500HCID 54012500, compound

Product 1

HCID 21704995HCID 21704995, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1 g (2.5 mmole) 5-(4-[2-(4-methoxycarbonylaminophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione was mixed with Pd/C (5%) and hydrogenated in ethyl acetate for 4 hours at room temperature. The catalyst was filtered off through celite and the solvent was evaporated in vacuo. All of the starting material was not consumed so the hydrogenation was restarted as above. The catalyst was filtered off through celite and the solvent was evaporated in vacuo. The crude product was purified by crystallization in diethyl ether to give 0.47 g (yield 47%) of the desired product.

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. customthe solvent was evaporated in vacuo
  3. customAll of the starting material was not consumed so the hydrogenation
  4. filtrationThe catalyst was filtered off through celite
  5. customthe solvent was evaporated in vacuo
  6. customThe crude product was purified by crystallization in diethyl ether

Sources & evidence

ORD record
ord-029773a9b749428db08c0b952b2e9d7c
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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