Reaktion #74859

Reaktionsgleichung

chloroacetyl chloride

pyridine

3-(2,6-dimethylphenylamino)-2-butanone O-methyloxime

pyridine

chloroacetyl chloride

→

3-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone O-methyloxime

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction temperature rose to about 50°-58° C. during the addition
2. 2
   TemperaturThe reaction mixture was then cooled
3. 3
   Waschenwashed with water
4. 4
   Waschenwashed with 5% aqueous sodium bicarbonate solution
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under reduced pressure

Vorschrift

A sample of 54.2 g (0.048 mol) chloroacetyl chloride and a sample of 34.8 g (0.44 mol) pyridine was added over a 25-minute period to a solution of 97.0 g (0.44 mol) 3-(2,6-dimethylphenylamino)-2-butanone O-methyloxime maintained at 45° C. in 500 ml benzene. The pyridine was added slightly faster than the chloroacetyl chloride. The reaction temperature rose to about 50°-58° C. during the addition. The reaction mixture was then cooled, washed with water, washed with 5% aqueous sodium bicarbonate solution, stirred with silica gel, filtered and evaporated under reduced pressure to give 111.5 g of 3-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone O-methyloxime, as an oil. The infrared spectrum of the product showed carbonyl absorption at 5.9 micron and O--CH3 absorption at 9.5 micron. The product is tabulated in Table I as Compound No. 5-B.

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