Chloroacetic Acid → 2-Chloro-N-methyl-N-phenylacetamide

Participants

Reaction Steps

76.75g (0.50 moles) of phosphoryl chloride and 107g (1.00 moles) of N-methyl aniline were added to 99.2g (1.05 moles) of monochloracetic acid. Alternate additions of 10% of the total amount of each of the N-methyl aniline and of the phosphoryl chloride were made with stirring at a temperature of 60° to 70°C over a period of 75 minutes. The reaction mixture was then stirred at 100° to 110°C for 4 hours, after which the reaction mixture was cooled to 70° to 80°C and then poured into warm water. The aqueous suspension was stirred vigorously whilst cooling until the product crystallised and then cooled further until the temperature reached 30° to 35°C. The precipitated crystalline product was separated from the aqueous phase by filtration and then washed with water. The washed product was dried in an oven at a temperature of 50° to 60°C. 157g of dry off-white crystals of N-methyl chloro acetanilide having a melting point of 69°C were obtained. The yield was 85.5% based on the theoretical yield from the N-methyl aniline in the starting material.

Provenance & Evidence