Sodium Bicarbonate → N-{4-[4-(4-Nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide

HRID 2232404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232404
Cl.[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][N:21]=1.C(=O)(O)[O-].[Na+]>C(O)CCC>[N+:26]([C:24]1[CH:23]=[CH:22][N:21]=[C:20]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:12][CH:13]=3)[CH2:3][CH2:4]2)[CH:25]=1)([O-:28])=[O:27]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 7351522-Chloro-4-nitropyridineHCID 18759927N-[4-(piperazin-1-yl)phenyl]methanesulfonamide hydrochloride

Produkt 1

HCID 21283530N-{4-[4-(4-Nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of the product of (iii) above (1.46 g), 2-chloro-4-nitropyridine (0.79 g) and sodium bicarbonate (1.26 g) in n-butanol (30 ml) were heated under reflux with stirring for 24 hours and then cooled and filtered. The solid was washed with methanol and the combined filtrate and washings were evaporated to give a gum that was chromatographed on silica gel. Elution with dichloromethane, gradually increasing the polarity to dichloromethane/methanol (4:1) gave a mixture of the desired product, together with some N-{4-[4-(2-chloropyrid-4-yl)piperazin-1-yl]phenyl}methanesulphonamide biproduct, as a solid. The solid was crystallised four times from methanol to give pure N-{4-[4-(4-nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide (0.36 g), m.p. 182°-183° C. Found: C,50.90; H,5.07; N,18.51. C16H19N5O4S requires: C,50.91; H,5.07; N,18.56%.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe solid was washed with methanol
  6. customthe combined filtrate and washings were evaporated
  7. customto give a gum that
  8. customwas chromatographed on silica gel
  9. washElution with dichloromethane
  10. temperaturegradually increasing the polarity to dichloromethane/methanol (4:1)
  11. customgave

Quellen und Nachweise

ORD-Eintrag
ord-1b3324e54c4e494ebe4ba925457e714b
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788196

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