Chloroacetyl chloride → 2-chloro-N-ethyl-N-(2,2,2-trifluoroethyl)acetamide

To a cooled (0° C.) solution of N-ethyl-2,2,2-trifluoroethanamine hydrochloride, (0.45 g, 2.8 mmol) in DCM (10 mL) was added triethylamine (1.6 mL, 11.2 mmol) followed by 2-chloroacetyl chloride (0.22 mL, 2.8 mmol). The reaction was warmed to RT and stirred for 2 h. The reaction mixture was concentrated, redissolved in EtOAc (20 mL) and washed with brine (25 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to yield 0.6 g of crude product which was further purified by flash column chromatography using 1:1 EtOAc:hexanes as the eluent. 0.5 g of 2-chloro-N-ethyl-N-(2,2,2-trifluoroethyl)acetamide, (yield: 88%) was isolated.

1. concentrationThe reaction mixture was concentrated
2. dissolutionredissolved in EtOAc (20 mL)
3. washwashed with brine (25 mL)
4. dry with materialThe organic layer was dried over anhydrous Na2SO4
5. concentrationconcentrated
6. customto yield 0.6 g of crude product which
7. customwas further purified by flash column chromatography

ORD record

ord-edee8878a93c4717a9b63ea519d65f5a

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08133998B2