Potassium Acetate → 4-(4-Chlorophenylsulfonylmethyl)thiazole

Temperature

70 °C

To 1-propanol (10 ml) were added sodium 4-chlorobenzenesulfinate (359 mg, 1.81 mmol), 4-(chloromethyl)thiazole hydrochloride (307 mg, 1.81 mmol) and potassium acetate (354 mg, 3.61 mmol) and the mixture was stirred at 70° C. for 21 hours. After cooling the reaction mixture to room temperature, the solvent was concentrated under reduced pressure. Ethyl acetate was added to the residue. The mixture was washed successively with water and brine and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate eluate (=3:2) was concentrated under reduced pressure. The resulting solid was washed with hexane-ether and then collected by filtration, whereby the title compound (154 mg, 31%) was obtained as a white powder.

1. temperatureAfter cooling the reaction mixture to room temperature
2. concentrationthe solvent was concentrated under reduced pressure
3. additionEthyl acetate was added to the residue
4. washThe mixture was washed successively with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customthe fraction obtained from the hexane
9. concentrationethyl acetate eluate (=3:2) was concentrated under reduced pressure
10. washThe resulting solid was washed with hexane-ether
11. filtrationcollected by filtration, whereby the title compound (154 mg, 31%)
12. customwas obtained as a white powder

ORD record

ord-ac402ff9e48b41a1a6156934e355047b

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2