Water → 4-bromo-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide

HRID 1635705

Reaktionsgleichung

Reaktionsgleichung von HRID 1635705
C(=O)([O-])[O-].[Ca+2].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH3:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([CH3:32])[C:24]=1[S:25]([CH2:28][N+:29]([O-:31])=[O:30])(=[O:27])=[O:26])[NH2:21].O>O1CCCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:21][C:20]2[CH:19]=[C:18]([CH3:17])[C:24]([S:25]([CH2:28][N+:29]([O-:31])=[O:30])(=[O:27])=[O:26])=[C:23]([CH3:32])[CH:22]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 10112Calcium CarbonateHCID 195716Ici 222155

Produkt 1

HCID 186765404-bromo-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamideAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.0 g (20.0 mmol) of calcium carbonate and 3.8 g (14.9 mmol) of 4-bromobenzenesulphonyl chloride are successively added to a mixture of 2.4 g (9.83 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 45 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 20 h at room temperature and is then refluxed for 48 h. After cooling, it is poured into 400 ml of water and extracted with methylene chloride. The combined organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure. The oily residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) to give 1.1 g (24%) of 4-bromo-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide.

Aufarbeitung

  1. temperatureis then refluxed for 48 h
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe oily residue obtained
  7. customis purified by chromatography on a column of silica (eluent: methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-b40e833edb224f349c1bd9d6ac3cf4fd
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509499B1

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