Ethanol → 1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide

HRID 1891015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891015
C(O)C.[CH3:4][N:5]([CH3:19])[S:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)(=[O:8])=[O:7].C(=O)([O-])[O-].[Na+].[Na+]>Cl.[Fe].O>[NH2:16][C:12]1[CH:11]=[C:10]([CH2:9][S:6]([N:5]([CH3:19])[CH3:4])(=[O:8])=[O:7])[CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 28632733N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide

Produkt 1

HCID 432562151-(3-aminophenyl)-N,N-dimethylmethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred mixture of iron powder (0.5 g), ethanol (20 ml), water (1 ml) and concentrated hydrochloric acid (5 drops) at reflux was added N,N-Dimethyl-C-(3-nitro-phenyl)-methanesulfonamide (0.5 g). The mixture was then heated under reflux for a further 2 hours then basified with excess sodium carbonate solution, cooled to 60° C., then filtered. The filter cake washed with ethanol and the filtrate evaporated. The crude product was partitioned between ethyl acetate and water, separation and evaporation of the organic phase gave C-(3-Amino-phenyl)-N,N-dimethyl-methanesulfonamide, 0.4 g, sufficiently pure to use.

Aufarbeitung

  1. temperatureat reflux
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for a further 2 hours
  4. filtrationfiltered
  5. washThe filter cake washed with ethanol
  6. customthe filtrate evaporated
  7. customThe crude product was partitioned between ethyl acetate and water, separation and evaporation of the organic phase

Quellen und Nachweise

ORD-Eintrag
ord-6d35f2d12fa04d2283f443769a77ea70
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507498B2

Notizen zur Reaktion

Wird geladen…