Aniline → Chloroacetanilide

Participants

Reaction Conditions

Reaction Steps

Aniline (93.1 g; 1.00 mole) was dissolved in toluene (750 ml), 10 % NaOH (750 ml) was added and the stirred mixture was cooled to 0°C. Chloroacetyl chloride (197 g; 1.75 mole) was added dropwise during 45 minutes while keeping the temperature below 10°C. Stirring was continued at room temperature for about one hour. The precipitated crystalline 2-chloro-N-phenylacetamide was filtered off, washed on the filter with cold toluene and dried in vacuo at 60°C. Yield: 151 g (90.0 %); m.p. 134°-136°C.

Provenance & Evidence