Anthranilic Acid → Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-

Participants

Reaction Conditions

Reaction Steps

99.26 g of anthranilic acid was added to 830 g of water, the resulting mixture was heated at 75° C. and 165.3 g of p-toluenesulfonyl chloride was added thereto over 30 minutes with stirring. 495 g of 28% aqueous solution of sodium hydroxide was added dropwise and the mixture was stirred at 80° C. for one hour. The reaction mixture was added dropwise to a mixed solution of 360 g of 35% hydrochloric acid and 270 g of water at 70 to 80° C. and stirred for one hour. After cooling to 30° C., the mixture was filtered, the resulting crystals were washed with water, and the wet crystals were heated and solved in 750 g of 1-propanol to obtain a solution. After cooling to a room temperature, the solution was filtered, the resulting crystals were washed with 1-propanol, and dried under a reduced pressure to obtain 175 g of N-tosyl anthranilic acid.

Provenance & Evidence