Hydrochloric Acid → 3-methyl-N-(phenylthioacetyl)anthranilic acid

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Reaction Steps

Benzenethiol and butyl bromoacetate were reacted by a conventional method and then hydrolyzed to obtain α-phenylthioacetatic acid. α-phenylthioacetatic acid was reacted with thionyl chloride by a convention method to obtain α-phenylthioacetyl chloride. 3-Methylanthranilic acid 5g (33 mmol) was dissolved in 10% aqueous sodium hydroxide solution 27 ml and to this solution, α-phenylthioacetyl chloride 5.5 ml (33 mmol) was added dropwise at 0° C. The resulting solution was stirred at room temperature for 1 hour and neutralized with 10% hydrochloric acid solution. Deposited crystals were collected by filtration and recrystallized from ethanol and water to obtain 3-methyl-N-(phenylthioacetyl)anthranilic acid (melting point: 148° to 150° C.) 8.8 g (yield: 89%).

Provenance & Evidence