反应详情

4-Amino-3-chlorobenzonitrile (1.50 g (9.83 mmol)) was dissolved in 5.0 ml of pyridine. To this, p-toluenesulfonyl chloride (1.90 g (9.97 mmol)) was added under cooling with ice and with stirring. After stirring for 18 hours at room temperature, water (100 ml) was added to the reaction mixture to bring about separation of crystals. The crystals were filtered, washed with water and then dissolved in an aqueous solution of sodium hydroxide. The resulting solution was washed with diethyl ether, and the water layer was made acidic again with hydrochloric acid and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.65 g (55%) of 2′-chloro-4′-cyano-p-toluenesulfonanilide as white crystals.

1. temperatureunder cooling with ice
2. stirringAfter stirring for 18 hours at room temperature
3. customto bring about separation of crystals
4. filtrationThe crystals were filtered
5. washwashed with water
6. dissolutiondissolved in an aqueous solution of sodium hydroxide
7. washThe resulting solution was washed with diethyl ether
8. extractionextracted with chloroform
9. dry with materialThe extract was dried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure