反应详情

155 mg (0.627 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 10 mL of reagent grade acetone. 2-Bromo-1-(4-chloro-3-methylphenyl)ethan-1-one (0.658 mmol; 163 mg) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and the reaction mixture was concentrated and dissolved in 50 mL of CH2Cl2. The organic layer was washed with 50 mL of 1N HCl (aq.), dried over sodium sulfate and concentrated. The crude product was purified on a 1 mm silica plate eluting with 20% ethyl acetate/hexane to afford 168 mg (68% yield) of methyl 4-[4-(4-chloro-3-methylphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

1. temperatureto reflux for 3 h
2. temperatureto cool
3. concentrationthe reaction mixture was concentrated
4. dissolutiondissolved in 50 mL of CH2Cl2
5. washThe organic layer was washed with 50 mL of 1N HCl (aq.)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe crude product was purified on a 1 mm silica plate
9. washeluting with 20% ethyl acetate/hexane