Hydrochloric Acid → HCID 23333570, compound

Participants

Reaction Steps

Ethyl iodide (35.1 g) was gradually added dropwise to a mixed liquid of ethyl 4-(N-benzenesulfonyl)aminophenylacetate (60 g), potassium carbonate (39 g), and acetone (500 ml) while stirring and refluxing it. Then, the mixture was refluxed for 2 hours with stirring. The mixture was cooled, and the precipitated crystals were removed by filtration. The filtrate was distilled for removal of the solvent. The residue was dissolved in benzene, and the solution was washed in water, followed by drying over magnesium sulfate. The dried product was distilled to remove the solvent, and the residue was recrystallized from n-hexane to obtain 64.3 g (m.p. 99.8°-100.8° C.) of ethyl 4-(N-ethyl-N-benzeneslfonyl) aminophenylacetate as prismatic crystals. Subsequently, 48% hydrobromic acid (380 ml) and phenol (64.3 g) were added to the ethyl ester, and the mixture was refluxed for 4 hours. While being cooled, the refluxed mixture was washed with benzene, and distilled to remove the aqueous layer. To the residue was added benzene, and the mixture was distilled to remove moisture and crude 4-(N-ethyl)aminophenylacetic acid hydrobromide was obtained. Then, ethanol (300 ml) was added to the hydrobromide. While being cooled, the mixture was saturated with hydrogen chloride gas. With the introduction of hydrogen chloride gas, the mixture was refluxed for 4 hours. After the reaction, the solvent was distilled off. The residue was dissolved in water, and the solution was washed with ether. The aqueous layer was neutralized with potassium carbonate while cooling the layer with ice, and extracted with ether. The extract was dried over magnesium sulfate. After the solvent was distilled off, the residue was vacuum-distilled to obtain 26.8 g of the desired N-ethyl-4-ethoxycarbonylmethylaniline as a fraction boiling at 112.5° C. at 0.02 mmHg.

Provenance & Evidence