HCID 86754366, compound → HCID 69830767, compound

HRID 1584296Notes

Reaction equation

HRID 1584296 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:24][CH:25]=1)[CH:6]=[CH:7][CH:8]=[C:9]1[O:13][C:12](=[O:14])[NH:11][C:10]1=[O:15]>[C].[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[O:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[S:24][CH:25]=1

Participants

4

Reactant 1

HCID 86754366HCID 86754366, compound

Product 1

HCID 69830767HCID 69830767, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[3-methoxy-4-(2-phenyl-4-thiazolylmethoxy)cinnamylidene]-2,4-oxazolidinedione (0.76 g), palladium-carbon (5%, 1.0 g) and tetrahydrofuran (THF) (100 ml) was subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-ethyl acetate (4:1), 5-[3-[3-methoxy-4-(2-phenyl-4-thiazolylmethoxy)phenyl]propyl]-2,4-oxazolidinedione (0.25 g, 32%) was obtained. Recrystallization of the product from ethyl acetate-hexane gave colorless prisms, m.p.96-97° C.

Workup

  1. customwas subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washFrom the fraction eluted with chloroform-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-540e31b44ad04e1284642f75755a68b1
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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