1,3-Dichloroacetone → 4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole

Temperature

85 °C

A mixture of 4-chlorothiobenzamide (0.5 g, 2.9 mmol) and 1,3-dichloroacetone (0.4 g, 3.18 mmol) in EtOH-THF (20 mL-10 mL) was heated to 85° C. for 10 h. The reaction mixture was cooled to room temperature and quenched with 10% NaHCO3 solution. The organic product was extracted with EtOAc and the organic layer was washed with H2O and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 3-5% EtOAc in petroleum ether) to afford 4-(chloromethyl)-2-(4-chlorophenyl)thiazole (0.55 g, yield 77%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.91-7.88 (m, 2H), 7.44-7.41 (m, 2H), 7.33 (s, 1H), 4.75 (s, 2H). MS (ESI) m/z: Calculated for C10H7Cl2NS: 242.97. found: 244.0 (M+H)+.

1. temperatureThe reaction mixture was cooled to room temperature
2. customquenched with 10% NaHCO3 solution
3. extractionThe organic product was extracted with EtOAc
4. washthe organic layer was washed with H2O and brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was removed under reduced pressure
7. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 3-5% EtOAc in petroleum ether)

ORD record

ord-1a91a020b947433dadf2144129fe1fac

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901156B2