5-Ethynyl-4-phenyl-thiazol-2-ylamine → 2-Thiazolamine, 5-ethyl-4-phenyl-

HRID 1009047Notes

Reaction equation

HRID 1009047 reaction equation
[C:1]([C:3]1[S:7][C:6]([NH2:8])=[N:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[CH:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[S:7][C:6]([NH2:8])=[N:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 866309595-Ethynyl-4-phenyl-thiazol-2-ylamine

Product 1

HCID 1475602-Thiazolamine, 5-ethyl-4-phenyl-Yield 74.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The above prepared 5-ethynyl-4-phenyl-thiazol-2-ylamine (0.665 g, 3.321 mmol) was dissolved in 12 mL of ethyl acetate and hydrogenated over 0.330 g of Pd on charcoal (10%) at atmospheric pressure and ambient temperature over night. Filtration over a pad of Celite and evaporation off all solvents, followed by flash chromatography (SiO2, hexane/ethyl acetate=65/35), yielded 0.505 g of the title product as yellow viscous oil.

Workup

  1. filtrationFiltration
  2. customover a pad of Celite and evaporation off all solvents

Sources & evidence

ORD record
ord-368be31b240c4e19958fc79b921b7f23
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

Loading…