Pyridine → N-isopropyl-N-(4-oxobutyl)-3,4-dichlorobenzenesulfonamide

HRID 2290954

Reaktionsgleichung

Reaktionsgleichung von HRID 2290954
N1C=CC=CC=1.[CH:7]([N:10]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[S:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)(=[O:13])=[O:12])([CH3:9])[CH3:8]>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[CH:7]([N:10]([CH2:22][CH2:23][CH2:24][CH:25]=[O:26])[S:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)(=[O:12])=[O:13])([CH3:9])[CH3:8]

Komponenten

5

Edukt 2

HCID 1049PyridineHCID 13770966N-isopropyl-N-(4-hydroxybutyl)-3,4-dichlorobenzenesulfonamide

Produkt 1

HCID 13770967N-isopropyl-N-(4-oxobutyl)-3,4-dichlorobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10219390chromium (VI) trioxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Pyridine-chromic acid complex was prepared by adding chromium trioxide (26.4 g, 94 m. moles) to pyridine (41.76 g) in methylene chloride (660 ml). The reaction mixture was stirred at room temperature for 3/4 hours. Then N-isopropyl-N-(4-hydroxybutyl)-3,4-dichlorobenzenesulfonamide prepared in the preceding paragraph (15.01 g) in methylene chloride (150 ml) was added all at once. After 1/2 hour the liquid was decanted and washed with 5% aqueous NaOH, 5% aqueous HCl, 5% aqueous NaHCO3 and finally brine. After removal of solvent there was obtained N-isopropyl-N-(4-oxobutyl)-3,4-dichlorobenzenesulfonamide as a dark oil (9.01 g) which started to nicely crystallize but was used below without further purification.

Aufarbeitung

  1. customPyridine-chromic acid complex was prepared
  2. additionwas added all at once
  3. customAfter 1/2 hour the liquid was decanted
  4. washwashed with 5% aqueous NaOH, 5% aqueous HCl, 5% aqueous NaHCO3 and finally brine
  5. customAfter removal of solvent there

Quellen und Nachweise

ORD-Eintrag
ord-691aea981ce346a3b0539ec7acdd382e
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618711

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