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

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

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)+