4-Bromophenacyl bromide → 4-(4-Bromophenyl)-2-methyl-1,3-thiazole

HRID 396783Notes

Reaction equation

HRID 396783 reaction equation
[CH:1]1[C:6]([C:7]([CH2:9]Br)=O)=[CH:5][CH:4]=[C:3]([Br:11])[CH:2]=1.[C:12]([NH2:15])(=[S:14])[CH3:13].[OH-].[Na+]>O1CCOCC1>[Br:11][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[N:15]=[C:12]([CH3:13])[S:14][CH:9]=2)=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 14798Sodium HydroxideHCID 2723949Thioacetamide

Product 1

HCID 6201384-(4-Bromophenyl)-2-methyl-1,3-thiazoleYield 103.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2,4-dibromoacetophenone (5 g, 18 mmol) in dioxane (180 ml) was added thioacetamide (6.76 g, 90 mmol), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, and made basic by addition of 2N NaOH aqueous solution. The whole was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (4.73 g, 99% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. extractionThe whole was extracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:5)

Sources & evidence

ORD record
ord-cd10578e17b44255bc5b5e69c5dd548d
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

Loading…