反应详情

A solution of 4-acetamido-3-chlorobenzenesulphonyl chloride (2.68 g, 10.0 mmol), sulphanilamide (2.06 g, 12.0 mmol), dimethylaminopyridine (1.22 g, 10.0 mmol) and pyridine (2.40 ml, 10.0 mmol) in EtOAc (150 ml) was stirred at ambient temperature for 3 days. The solution was washed with 1.0M aqueous hydrochloric acid and brine, dried and evaporated to dryness. The residue was dissolved in ethanol (100 ml) and 2M aqueous sodium hydroxide (22.1 ml) was added. The mixture was heated at reflux for 4 hours and then cooled to ambient temperature and evaporated to dryness. Water (25 ml) was added to the residue and the solution was neutralised to pH 7.0 by the addition of 1M aqueous hydrochloric acid. The aqueous solution was extracted with EtOAc, the EtOAc extracts washed with brine, dried and evaporated to give, as a solid, the title compound (2.34 g, 6.5 mmol). M.p. 197°-198°; NMR: 6.3 (s, 2H), 6.8 (d, 1H), 7.2 (s, 2H), 7.25 (d, 2H), 7.4 (dd, 2H), 7.55 (d, 1H), 7.65 (d, 2H); MS: 360.

1. washThe solution was washed with 1.0M aqueous hydrochloric acid and brine
2. customdried
3. customevaporated to dryness
4. dissolutionThe residue was dissolved in ethanol (100 ml)
5. addition2M aqueous sodium hydroxide (22.1 ml) was added
6. temperatureThe mixture was heated
7. temperatureat reflux for 4 hours
8. customevaporated to dryness
9. additionWater (25 ml) was added to the residue
10. additionthe solution was neutralised to pH 7.0 by the addition of 1M aqueous hydrochloric acid
11. extractionThe aqueous solution was extracted with EtOAc
12. washthe EtOAc extracts washed with brine
13. customdried
14. customevaporated
15. customto give, as a solid