N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide → N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide

HRID 1892469Notes

Reaction equation

HRID 1892469 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[C].[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86649975N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide

Product 1

HCID 86649977N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide (932.3 mg, 3.58 mmol) in ethyl acetate (50 ml) was added 10% palladium carbon, and the mixture was hydrogenated at room temperature and atmospheric pressure. After the completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, dichloromethane:methanol=40:1→20:1) to give N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide (771.3 mg, 2.94 mmol, yield 82.1%) as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter the completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, dichloromethane:methanol=40:1→20:1)

Sources & evidence

ORD record
ord-e1a983c931a64febbb025327c5369e87
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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