反应详情

A solution of 1.7 g (14.8 mmol) of methanesulphonyl chloride in 5 ml of anhydrous tetrahydrofuran is added dropwise to a solution, maintained under a nitrogen atmosphere, of 2.7 g (11.0 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline and 1.6 g (20.2 mmol) of pyridine, dried over potassium hydroxide, in 50 ml of anhydrous tetrahydrofuran. The mixture is stirred for 6 h 30 min at room temperature and is then refluxed for 4 h. 1.1 g (9.60 mmol) of methanesulphonyl chloride are then added and refluxing is continued for 1 h 30 min. A further 1.1 g (9.60 mmol) of methanesulphonyl chloride are added and refluxing is continued for 4 h. After cooling, the reaction medium is poured into ice-cold water and extracted with methylene chloride. The combined organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue obtained is crystallized from a cooled mixture of hexane and methylene chloride and is purified by recrystallization from a mixture of hexane and ethyl acetate, to give 1.1 g (yield=22%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]methanesulphonamide containing 14 mol % of ethyl acetate.

1. dry with materialdried over potassium hydroxide, in 50 ml of anhydrous tetrahydrofuran
2. temperatureis then refluxed for 4 h
3. temperaturerefluxing
4. waitis continued for 1 h 30 min
5. temperaturerefluxing
6. waitis continued for 4 h
7. temperatureAfter cooling
8. additionthe reaction medium is poured into ice-cold water
9. extractionextracted with methylene chloride
10. dry with materialThe combined organic extracts are dried over sodium sulphate
11. concentrationconcentrated to dryness under reduced pressure
12. customThe residue obtained
13. customis crystallized from a cooled mixture of hexane and methylene chloride
14. customis purified by recrystallization from a mixture of hexane and ethyl acetate