5-[[3-(1,1-Dimethylethyl)-4-hydroxy-5-methylphenyl]methylene]-4-thiazolidinone → HCID 18936445, compound

HRID 2952Notes

Reaction equation

HRID 2952 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:13]=[C:14]2[S:18][CH2:17][NH:16][C:15]2=[O:19])[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:4])[CH3:3]>O1CCCC1.[Pd]>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH2:13][CH:14]2[S:18][CH2:17][NH:16][C:15]2=[O:19])[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 537701815-[[3-(1,1-Dimethylethyl)-4-hydroxy-5-methylphenyl]methylene]-4-thiazolidinone

Product 1

HCID 18936445HCID 18936445, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.28 g of the compound of Example 61 in 30 ml of tetrahydrofuran was hydrogenated at 60 pounds per square inch in the presence of 1.12 g of 5% palladium on carbon overnight at 60° C. The reaction mixture was filtered and evaporated to dryness. The resulting residue was dissolved in 3.5 ml of a 1:1.5 ethyl acetate/hexane solution and loaded onto a silica gel chromatography column. Elution with 40% ethyl acetate in hexane produced fractions which, upon evaporation to dryness, provided 0.05 g of title compound. m.p. 64°-68° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. dissolutionThe resulting residue was dissolved in 3.5 ml of a 1:1.5 ethyl acetate/hexane solution
  4. washElution with 40% ethyl acetate in hexane produced fractions which
  5. customupon evaporation to dryness

Sources & evidence

ORD record
ord-4349083726d1496ca8ab1e9e85158d89
Source dataset
uspto-grants-1998_03
Patent number
US05731336

Reaction notes

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