Triethylamine → 2-Chloro-N,N-dimethyl-5-nitrobenzene-1-sulfonamide

HRID 375676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375676
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].Cl.[CH3:16][NH:17][CH3:18].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:16][N:17]([CH3:18])[S:11]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:13])=[O:12]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Produkt 1

HCID 201055802-Chloro-N,N-dimethyl-5-nitrobenzene-1-sulfonamideAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 80 g of 2-chloro-5nitrobenzenesulfonyl chloride (Example A-1 above) in 200 ml of methylene chloride heated to reflux, was slowly added a solution of 30 g of dimethylamine hydrochloride in 30 ml of water followed by a dropwise addition of triethylamine. After completion of the addition, the reaction mixture was refluxed for 20 minutes, cooled to room temperature and concentrated by rotatory evaporation. The residue was treated with water and the resulting solid was filtered and recrystallized from ethanol, affording 61 g of the title compound, mp 138°-140° C.

Aufarbeitung

  1. temperatureto reflux
  2. additionAfter completion of the addition
  3. temperaturethe reaction mixture was refluxed for 20 minutes
  4. concentrationconcentrated by rotatory evaporation
  5. additionThe residue was treated with water
  6. filtrationthe resulting solid was filtered
  7. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a581d7caa220439bb85f561c8f550666
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486610

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