Reaction #66688

Reaction equation

2,4-dimethoxy aniline

triethylamine

Chloroacetyl chloride

→

2-Chloro-N-(2,4-dimethoxy-phenyl)-acetamide

Yield 99.2%

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 15 minutes at 0° C.
2. 2
   workup.STIRRINGstirred for an additional two hours during which time the reaction mixture
3. 3
   Temperatureto warm to room temperature
4. 4
   OtherThe reaction was quenched by addition of 1N HCl
5. 5
   OtherThe aqueous mixture was partitioned with EtOAc
6. 6
   Otherthe organic phase was separated
7. 7
   Dryingdried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated under reduced pressure

Procedure

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.

Source