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3-Nitrobenzamide → 1-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

HRID 1588032
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1588032
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][S:16]([CH3:15])(=[O:18])=[O:17])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 125763-NitrobenzamideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A solution of 3-nitrophenylcarboxamide (2 g) in 150 ml of dry tetrahydrofuran was cooled to 0° C. and treated with 609 mg of sodium hydride (60% oil dispersion). The reaction mixture was stirred for 20 minutes and then methanesulfonylchloride (1.18 ml) was introduced dropwise via syringe. After 5 minutes the reaction mixture became homogeneous and was warmed to room temperature and stirred overnight. The reaction mixture was diluted with 300 ml of ethyl acetate and was washed with brine. The organic extracts were dried, concentrated in vacuo, and the residue was chromatographed on silica gel (ethyl acetate then chloroform-methanol, 95:5 v/v) to yield 1.6 g of the title compound in pure form.

Aufarbeitung

  1. waitAfter 5 minutes the reaction mixture became homogeneous
  2. stirringstirred overnight
  3. washwas washed with brine
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-17ff4023f4b14d038157070b4c950e28
Quelldatensatz
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05220018

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