Chloroacetyl chloride → HCID 15174914, compound

To a stirred slurry of finely powdered isooxazolidine hydrochloride (H. King, J. Chem. Soc. 433,1942) (11.0 g) in dry ether (200 ml) at 0° C. was added triethylamine (28.0 ml) and a solution of chloroacetyl chloride (8.0 ml) in ether (50 ml). The reaction mixture was stirred for a further 4 hours, whilst the temperature rose to room temperature. The precipitate triethylamine hydrochloride was filtered off through diatomaceous earth and the filter bed washed well with ether. The combined ether solutions were evaporated to give N-chloroacetyl isooxazolidine as an oil (11.5 g) NMR (CDCl3) 2.38[quintet, 2H, CH2 ], 3.78[t,2H, NCH2 ], 4.05[t,2H, OCH2 ]and 4.22 [s,2H, ClCH2CO].

1. customrose to room temperature
2. filtrationThe precipitate triethylamine hydrochloride was filtered off through diatomaceous earth
3. washthe filter bed washed well with ether
4. customThe combined ether solutions were evaporated

ORD record

ord-058e5c4a27c645e7becd71851b9369ff

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04999377