Chloroacetyl chloride → 2-chloro-N-(5-chloropyridin-2-yl)acetamide

Chloroacetyl chloride (95.5 ml) is dissolved in dichloromethane (500 ml), and thereto is added dropwise a suspension of 2-amino-5-chloropyridine (128.6 g) and triethylamine (169 ml) in dichloromethane (1000 ml) under ice-cooling, and the reaction solution is warmed to room temperature, and stirred for 0.5 hours. The reaction solution is concentrated under reduced pressure, thereto is poured ice-water, and then the reaction mixture is extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and treated with activated charcoal. After filtration to remove insoluble materials, the filtrate is concentrated under reduced pressure and the resulting residue is suspended in diisopropyl ether. The precipitates are collected by filtration, washed with diisopropyl ether and dried to give 2-chloro-N-(5-chloropyridin-2-yl)acetamide (153.4 g).

1. additionis added dropwise
2. temperaturecooling
3. concentrationThe reaction solution is concentrated under reduced pressure
4. additionis poured ice-water
5. extractionthe reaction mixture is extracted with ethyl acetate
6. washThe organic layer is washed with saturated brine
7. dry with materialdried over sodium sulfate
8. additiontreated with activated charcoal
9. filtrationAfter filtration
10. customto remove insoluble materials
11. concentrationthe filtrate is concentrated under reduced pressure
12. filtrationThe precipitates are collected by filtration
13. washwashed with diisopropyl ether
14. customdried

ORD record

ord-b62eb539d4684876bd3c42f6b68673aa

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531537B2