Tert-Butylamine → N-tert-butyl-2-chloroacetamide

To a cooled (0° C.) solution of tert-butyl amine (5.25 mL, 50 mmol) in DCM (40 mL) was added triethylamine (14 mL, 101 mmol) followed by chloro acetylchloride (3.98 mL, 50.3 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. The organic layer was dried over anhydrous Na2SO4 and concentrated to yield 5.39 g of crude product which was further purified by flash column chromatography using 7:3 Pet. Ether: EtOAc as the eluant. Pure N-tert-butyl-2-chloroacetamide (3.65 g) was isolated.

1. concentrationThe reaction mixture was concentrated
2. dissolutionredissolved in EtOAc (20 mL)
3. washwashed with brine
4. dry with materialThe organic layer was dried over anhydrous Na2SO4
5. concentrationconcentrated
6. customto yield 5.39 g of crude product which
7. customwas further purified by flash column chromatography

ORD record

ord-62c3ed11f0cf4a2686fa2eb2436c7965

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08133998B2