5-[4-(4-(2-Amino-2-methoxycarbonylethyl) phenoxy)benzilidene]thiazolidin-2,4-dione → 5-[4-(4-(2-Amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione

HRID 1007286Notes

Reaction equation

HRID 1007286 reaction equation
[NH2:1][CH:2]([C:25]([O:27][CH3:28])=[O:26])[CH2:3][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:22]=[CH:21][C:12]([CH:13]=[C:14]3[S:18][C:17](=[O:19])[NH:16][C:15]3=[O:20])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1>CO>[NH2:1][CH:2]([C:25]([O:27][CH3:28])=[O:26])[CH2:3][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:22]=[CH:21][C:12]([CH2:13][CH:14]3[S:18][C:17](=[O:19])[NH:16][C:15]3=[O:20])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 730387895-[4-(4-(2-Amino-2-methoxycarbonylethyl) phenoxy)benzilidene]thiazolidin-2,4-dione

Product 1

HCID 99308555-[4-(4-(2-Amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione (0.7 g, 1.6 mmol) in methanol (20 ml) dry Pd/C (0.15 g) was added. After hydrogenating at 60 psi at 40° C. over night, the solution was filtered with Celite and evaporated under reduced pressure to yield quantitatively the title compound. This compound did not show melting in DSC but changes to black colour, in capillary and shrinks at 97-133° C. Compound 2.

Workup

  1. waitAfter hydrogenating at 60 psi at 40° C. over night
  2. filtrationthe solution was filtered with Celite
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a4f25d81bbfa44399d6a81a0f8d0f009
Source dataset
uspto-grants-2004_09
Patent number
US06794401B2

Reaction notes

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