Phenacyl bromide → 2-Methyl-4-phenyl-1,3-thiazole

HRID 2252069Notes

Reaction equation

HRID 2252069 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O>O1CCOCC1.C(OCC)(=O)C>[CH3:2][C:1]1[S:3][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 2723949Thioacetamide

Product 1

HCID 5843772-Methyl-4-phenyl-1,3-thiazoleYield 78%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Add thioacetamide (0.09 g, 1.2 mmol) to a solution of 2-bromoacetophenone (0.2 g, 1.0 mmol) in 30 mL dioxane. Stir at room temperature for 4 hours, dilute with ethyl acetate, wash sequentially with aqueous sodium carbonate (3×15 mL) and water (3×20 mL). Dry the organic phase over sodium sulfate, concentrate under reduced pressure, and subject the residue to silica gel chromatography, eluting with hexane containing 10% ethyl acetate to provide the desired compound in 78% yield. MS(ES+): m/z=176.1 (M+H)+

Workup

  1. washwash sequentially with aqueous sodium carbonate (3×15 mL) and water (3×20 mL)
  2. dry with materialDry the organic phase over sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. washeluting with hexane containing 10% ethyl acetate

Sources & evidence

ORD record
ord-eae25ef68811498fb5bd899673730c2e
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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