Water → alpha-acetyl-2,4-dichloro-N-(2,4-difluorophenyl)benzeneethanethioamide

Temperature

7.5 °C

2,4-Difluorophenyl isothiocyanate (0.27 mL, 2.0 mmol) was added to a stirred suspension of sodium hydride (60% in mineral oil) (112 mg, 2.8 mmol) in anhydrous tetrahydrofuran (4 mL) cooled in an ice-water bath under a nitrogen atmosphere. A solution of 1-(2,4-dichlorophenyl)-2-propanone (570 mg, 2.8 mmol) in tetrahydrofuran (4 mL) was added dropwise over 5 min. The resultant yellow solution was stirred at 5-10° C. for 1 h. Water (10 mL) was carefully added, and the reaction mixture was extracted with ethyl acetate (10 mL). The aqueous phase was acidified to pH 3 with 1 N aqueous HCl, then extracted with ethyl acetate (20 mL). The organic extract was washed with water (10 mL) and brine (10 mL), dried over MgSO4, and concentrated to leave a solid. The solid was triturated with hexanes/ethyl acetate (2:1), collected on a glass frit, and air-dried to give the title compound as a white solid (240 mg). MS: 373 amu (AP+).

1. temperaturecooled in an ice-water bath under a nitrogen atmosphere
2. extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
3. extractionextracted with ethyl acetate (20 mL)
4. extractionThe organic extract
5. washwas washed with water (10 mL) and brine (10 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customto leave a solid
9. customThe solid was triturated with hexanes/ethyl acetate (2:1)
10. customcollected on a glass frit
11. customair-dried

ORD record

ord-11d10ff2a24e44ca855f15d2845b82c7

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09107412B2