Pyridine → N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]methanesulphonamide

HRID 1635712

Reaktionsgleichung

Reaktionsgleichung von HRID 1635712
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[CH:8]=[C:9]([CH:11]=[C:12]([CH3:21])[C:13]=1[S:14]([CH2:17][N+:18]([O-:20])=[O:19])(=[O:16])=[O:15])[NH2:10].N1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[CH3:21][C:12]1[CH:11]=[C:9]([NH:10][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=[C:7]([CH3:6])[C:13]=1[S:14]([CH2:17][N+:18]([O-:20])=[O:19])(=[O:15])=[O:16]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chloride3×HCID 195716Ici 222155

Produkt 1

HCID 18676571N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]methanesulphonamideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-846c7060344a4060bcd4336ce8c272c8
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509499B1

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