Chloroacetyl chloride → 2-chloro-N-(2,4-dimethoxyphenyl)acetamide

Temperature

0 °C

A mixture of 2,4-dimethoxy aniline (30.6 g, 0.2 mol), triethylamine (27.9 mL, 0.2 mol) in 600 mL methylene chloride was stirred at 0° C. under nitrogen. Chloroacetyl chloride (16 mL, 0.2 mol) was added dropwise, and the reaction mixture was stirred for 15 minutes at 0° C., and then stirred for an additional two hours during which time the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 1N HCl, followed by saturated aqueous sodium bicarbonate. The aqueous mixture was partitioned with EtOAc, and the organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure to give 45.58 g of crude 2-Chloro-N-(2,4-dimethoxy-phenyl)-acetamide. MS (M+H)=230.

1. stirringthe reaction mixture was stirred for 15 minutes at 0° C.
2. stirringstirred for an additional two hours during which time the reaction mixture
3. temperatureto warm to room temperature
4. customThe reaction was quenched by addition of 1N HCl
5. customThe aqueous mixture was partitioned with EtOAc
6. customthe organic phase was separated
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customevaporated under reduced pressure

ORD record

ord-28c78f0b87814c96b80a9efd1ceacb5d

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524725B2