反应详情

To a mixture of 4′-cyano-2′-nitro-p-toluenesulfonanilide sodium salt (1330 g (3.92 mol)) and DMF (3000 ml), under heating in an oil bath kept at 110° C., isopropyl iodide (2019 g (11.8 mol)) was added over a period of 1.5 hours. After completion of the addition, the mixture was further heated at the same temperature with stirring for 3 hours, and then left to cool to room temperature. Water (1500 ml) was added to bring about separation of crystals. The crystals were filtered, washed with water, dried, and then suspended in diethyl ether. The suspension was stirred for 4 hours, and the insolubles were removed by filtration, the diethyl ether solution was washed with 0.1% aqueous sodium hydroxide solution to remove the remaining starting material, 4′-cyano-2′-nitro-p-toluenesulfonanilide. The diethyl ether layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give crude crystals which were, after washing with ethanol, recrystallized from ethyl acetate to give 124 g (8.8%) of the title compound as pale yellow crystals.

1. temperatureunder heating in an oil bath
2. customkept at 110° C.
3. additionAfter completion of the addition
4. temperaturethe mixture was further heated at the same temperature
5. waitleft
6. customto bring about separation of crystals
7. filtrationThe crystals were filtered
8. washwashed with water
9. customdried
10. stirringThe suspension was stirred for 4 hours
11. customthe insolubles were removed by filtration
12. washthe diethyl ether solution was washed with 0.1% aqueous sodium hydroxide solution
13. customto remove the
14. dry with materialThe diethyl ether layer was dried over anhydrous magnesium sulfate
15. filtrationfiltered
16. concentrationconcentrated under reduced pressure
17. customto give crude crystals which
18. washafter washing with ethanol
19. customrecrystallized from ethyl acetate