Thionyl Chloride → N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-5-chloro-3-(trifluoromethyl)pentanamide

Temperature

40 °C

To a solution of N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-5-hydroxy-3-(trifluoromethyl)pentanamide (1.2 g, 3.2 mmol) in 100 ml methylene chloride, was added thionyl chloride (0.24 ml) in one portion via pipette. The solution turned brown. It was heated to 40°-50° C. for about 7 hours, kept at room temperature for 64 hours, heated to 40° C. for 3 hours, then stirred at room temperature for 18 hours. Then additional thionyl chloride (0.1 ml) was added and heating to 40° C. was resumed for about 4 hours. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dried in vacuo (50° C.) and the resulting golden brown, semi-solid mixture was purified via flash chromatography (20 ml fractions, 2'×7' column, 1:9 ethyl acetate/hexanes) to yield a brown solid, m.p. of 57°-63° C.

1. temperatureIt was heated to 40°-50° C. for about 7 hours
2. temperatureheating to 40° C.
3. waitwas resumed for about 4 hours
4. temperatureThe reaction mixture was cooled to room temperature
5. customthe solvent was removed in vacuo
6. customThe residue was dried in vacuo (50° C.)
7. customthe resulting golden brown, semi-solid mixture was purified via flash chromatography (20 ml fractions, 2'×7' column, 1:9 ethyl acetate/hexanes)
8. customto yield a brown solid, m.p. of 57°-63° C.

ORD record

ord-d3e8a8aaa6574723997756a5a1c958ae

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05502027