5-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione → 5-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione

HRID 4397Notes

Reaction equation

HRID 4397 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13](=[O:30])[CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH:20]=[C:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1>[Pd].O1CCOCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13](=[O:30])[CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 539081335-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione

Product 1

HCID 137139365-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g), Pd-black (3 g) and dioxane (100 ml) was hydrogenated at 40° C. and at atmospheric pressure. After 4 hours, another Pd-black (3 g) was added and hydrogenation was continued for 4 hours. The catalyst was filtered off and the filtrate was concentrated to yield 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzyl}-2,4-thiazolidinedione (the same compound as that obtained in Example 48) as crystals (0.95 g, 94.1%). Recrystallization from ethyl acetate-hexane gave colorless needles, m.p. 168°-169° C.

Workup

  1. customwas hydrogenated at 40° C. and at atmospheric pressure
  2. waithydrogenation was continued for 4 hours
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c8eb97027f2c4870835f040d585e95f1
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

Loading…