Chloroacetyl chloride → DL-Alanine, N-(chloroacetyl)-N-(2,6-dimethylphenyl)-, methyl ester

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Reaction Steps

990.3 g (= 4.76 g-moles) of α-(2,6-dimethylanilino)-propionic acid methyl ester is mixed with 605 g (= 5.7 g-moles) of sodium carbonate in 2.5 liters of benzene (absolute). An amount of 455 ml (= 5.7 g-moles) of monochloroacetyl chloride is then added dropwise and sufficiently slowly to ensure that a temperature of 30°-35° in the reaction mixture is not exceeded. After stirring has been maintained overnight at room temperature, the mixture is filtered off, and the filtrate concentrated in a rotary evaporator at ca. 50°. The resulting residue is recrystallised from ligroin (boiling range 65°-90° ). The yield obtained is 1132 g (= 83.8% of theory) of final product, M.P. 92°-94° (compound No. 3).

Provenance & Evidence