反应详情

A solution of 4-acetamidothiophenol (8.35 g, 50.0 mmol), ethylene carbonate (5.5 g, 62.5 mmol) and sodium ethoxide (4.1 g, 60.0 mmol) in ethanol (250 ml) was heated at reflux overnight and then cooled to ambient temperature and evaporated to dryness. The residue was dissolved in diethyl ether (500 ml), washed with 1M aqueous hydrochloric acid and brine, dried and evaporated to dryness. The residue was dissolved in ethanol (120 ml) and 2M aqueous sodium hydroxide (60 ml) was added. The mixture was heated at reflux overnight 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 by the addition of 1M aqueous hydrochloric acid. The aqueous solution was extracted with EtOAc, the EtOAc extracts were washed with brine, dried and evaporated to dryness. The residue was dissolved in DCM (100 ml) and added to a solution of 4-acetamido-3-chlorobenzenesulphonyl chloride (5.5 g, 20.5 mmol), 4-dimethylaminopyridine (50 mg, 0.4 mmol) and pyridine (5.0 ml, 60 mmol) in DCM (100 ml). The mixture was stirred at ambient temperature overnight, the solution was evaporated to dryness, the residue dissolved in diethyl ether (450 ml), washed with 1M aqueous hydrochloric acid and brine, dried and evaporated to dryness. The residue was dissolved in ethanol (100 ml) and 2M aqueous sodium hydroxide (25 ml) was added. The mixture was heated at reflux overnight 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 by the addition of 1M aqueous hydrochloric acid. The aqueous solution was extracted with EtOAc, the EtOAc extracts were washed with brine, dried and evaporated to dryness. The residue was purified by column chromatography using 10% EtOAc in DCM to yield the title compound (1.53 g, 3.96 mmol). NMR: 1.0 (t, 3H), 3.0 (t, 2H), 3.3-3.5 (m, 4H), 6.2 (s, 2H), 6.75 (d, 1H), 7.0 (d, 2H), 7.2 (d, 2H), 7.3 (dd, 1H), 7.45 (d, 1H); MS: 385.

1. temperatureat reflux overnight
2. customevaporated to dryness
3. dissolutionThe residue was dissolved in diethyl ether (500 ml)
4. washwashed with 1M aqueous hydrochloric acid and brine
5. customdried
6. customevaporated to dryness
7. dissolutionThe residue was dissolved in ethanol (120 ml)
8. addition2M aqueous sodium hydroxide (60 ml) was added
9. temperatureThe mixture was heated
10. temperatureat reflux overnight
11. temperaturecooled to ambient temperature
12. customevaporated to dryness
13. additionWater (25 ml) was added to the residue
14. additionthe solution was neutralised to pH 7 by the addition of 1M aqueous hydrochloric acid
15. extractionThe aqueous solution was extracted with EtOAc
16. washthe EtOAc extracts were washed with brine
17. customdried
18. customevaporated to dryness
19. dissolutionThe residue was dissolved in DCM (100 ml)
20. customthe solution was evaporated to dryness
21. dissolutionthe residue dissolved in diethyl ether (450 ml)
22. washwashed with 1M aqueous hydrochloric acid and brine
23. customdried
24. customevaporated to dryness
25. dissolutionThe residue was dissolved in ethanol (100 ml)
26. addition2M aqueous sodium hydroxide (25 ml) was added
27. temperatureThe mixture was heated
28. temperatureat reflux overnight
29. temperaturecooled to ambient temperature
30. customevaporated to dryness
31. additionWater (25 ml) was added to the residue
32. additionthe solution was neutralised to pH 7 by the addition of 1M aqueous hydrochloric acid
33. extractionThe aqueous solution was extracted with EtOAc
34. washthe EtOAc extracts were washed with brine
35. customdried
36. customevaporated to dryness
37. customThe residue was purified by column chromatography