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Sodium Iodide → N'-Desaminomethylsulfonyl-N'-nitryl Dofetilide

HRID 1089697
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1089697
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:14][S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]Cl)=[CH:21][CH:20]=1)(=[O:17])=[O:16].C(=O)(O)[O-].[Na+].[I-].[Na+]>C(#N)C>[CH3:14][S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)=[CH:21][CH:20]=1)(=[O:17])=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 2794239N-methyl-4-nitrophenethylamineHCID 20086989N-[4-(2-Chloroethoxy)phenyl]-methanesulfonamide

Produkt 1

HCID 19915717N'-Desaminomethylsulfonyl-N'-nitryl DofetilideAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A suspension of N-methyl-4-nitrophenethylamine (1.1 g), 2-(4-methanesulphonamidophenoxy)ethyl chloride (1.5 g), sodium bicarbonate (0.5 g) and sodium iodide (0.9 g) in acetonitrile (100 ml) was stirred at reflux for 4 days. On evaporation to dryness the resultant oil was partitioned between 2N aqueous sodium bicarbonate solution and methylene chloride. After two further extractions with methylene chloride, the organic portions were combined, washed with saturated brine solution, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The resultant brown oil was chromatographed on silica ("Kieselgel 60"--Trade Mark) eluting with ethyl acetate followed by collection and evaporation of suitable fractions to give the title compound as a yellow solid, (0.9 g).

Aufarbeitung

  1. temperatureat reflux for 4 days
  2. customOn evaporation to dryness the resultant oil
  3. customwas partitioned between 2N aqueous sodium bicarbonate solution and methylene chloride
  4. extractionAfter two further extractions with methylene chloride
  5. washwashed with saturated brine solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resultant brown oil was chromatographed on silica ("Kieselgel 60"--Trade Mark)
  10. washeluting with ethyl acetate
  11. customfollowed by collection and evaporation of suitable fractions

Quellen und Nachweise

ORD-Eintrag
ord-9c7d2b8325c745c3b1ebf6d2a35c0572
Quelldatensatz
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05079248

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