Thionyl Chloride → N-(4-{2-[4-(chloromethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide

To a solution of N-(4-{2-[3-fluoro-4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (196.6% mg, 0.668 mmol) in chloroform (10 ml) was added thionyl chloride (0.144 ml, 2.00 mmol), and the mixture was stirred at room temperature for 1 hr. Thionyl chloride (0.077 ml, 1.00 mmol) was added, and the mixture was stirred at room temperature for 1 hr and concentrated. Ethyl acetate (10 ml) was added to the residue, and the mixture was concentrated again under reduced pressure. The operation was performed 3 times to remove thionyl chloride azeotropically. A mixture of ethyl acetate (1 ml) and diisopropyl ether (10 ml) was added to the residue, and the precipitate was collected by filtration and dried under reduced pressure to give N-(4-{2-[4-(chloromethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (205.3 mg, 0.656 mmol, yield 98.3%) as a slightly yellow solid.

1. stirringthe mixture was stirred at room temperature for 1 hr
2. concentrationconcentrated
3. additionEthyl acetate (10 ml) was added to the residue
4. concentrationthe mixture was concentrated again under reduced pressure
5. customto remove thionyl chloride azeotropically
6. additionA mixture of ethyl acetate (1 ml) and diisopropyl ether (10 ml)
7. additionwas added to the residue
8. filtrationthe precipitate was collected by filtration
9. customdried under reduced pressure

ORD record

ord-482d7ea37e5e40369be0b3888b2635b9

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2