2-Propenamide, 3-phenyl- → HCID 86594853, compound

HRID 225776

Reaction equation

HRID 225776 reaction equation
[C:1]([NH2:11])(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1.Br[CH:35]([CH3:43])[C:36](=O)[CH2:37][C:38]([O:40][CH3:41])=[O:39]>O1CCCC1>[CH3:43][C:35]1[S:21][C:1]([CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][C:36]=1[CH2:37][C:38]([O:40][CH3:41])=[O:39]

Participants

5

Reactant 3

HCID 121352-Propenamide, 3-phenyl-HCID 87949Lawesson's reagentHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 86594853HCID 86594853, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cinnamamide (3.27 g) was dissolved in tetrahydrofuran (33 ml), and Lawesson's reagent (4.94 g) was added. The mixture was refluxed for 3 h and methyl 4-bromo-3-oxopentanoate (6.97 g) was added. The mixture was further refluxed for 11 h. Tetrahydrofuran was evaporated under reduced pressure and ethyl acetate (300 ml) was added to the obtained residue. The mixture was washed with water (200 ml) and then with saturated brine (200 ml), and dried (Na2SO4). Ethyl acetate was evaporated under reduced pressure and the obtained residue was purified by column chromatography to give methyl (5-methyl-2-styrylthiazole-4-yl)acetate (2.9 g).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. temperatureThe mixture was further refluxed for 11 h
  3. customTetrahydrofuran was evaporated under reduced pressure and ethyl acetate (300 ml)
  4. additionwas added to the obtained residue
  5. washThe mixture was washed with water (200 ml)
  6. dry with materialwith saturated brine (200 ml), and dried (Na2SO4)
  7. customEthyl acetate was evaporated under reduced pressure
  8. customthe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-a1c5a391e4c7465e901417098647f6eb
Source dataset
uspto-grants-2009_07
Patent number
US07557123B2

Linked notes

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