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

HRID 1892494Notes

Reaction equation

HRID 1892494 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][N:10]2[CH:14]=[CH:13][S:12][CH:11]2[NH:15][C:16](=[O:18])[CH3:17])=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)(=O)C.[C].[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][S:12][CH:11]2[NH:15][C:16](=[O:18])[CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 86650002N-{3-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide

Product 1

HCID 66863126N-{3-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamideYield 95.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{3-[2-(4-Hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide (1.900 g, 7.299 mmol) was dissolved in a mixture of ethyl acetate (300 ml) and acetic acid (50 ml), and 10% palladium carbon (760 mg, containing 50% water) was added. The mixture was hydrogenated at room temperature under 4-5 atm. After the completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate by heating, and recrystallized by cooling to give N-{3-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide (1.834 g, 6.993 mmol, yield 95.8%) as a white solid.

Workup

  1. additionwas added
  2. customwas hydrogenated at room temperature under 4-5 atm
  3. customAfter the completion of the reaction
  4. filtrationthe reaction mixture was filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. temperatureby heating
  8. customrecrystallized
  9. temperatureby cooling

Sources & evidence

ORD record
ord-69e87a4fd2b149bbafebdb8f53940587
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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