Ammonium Hydroxide → 4-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

HRID 1514859

Reaktionsgleichung

Reaktionsgleichung von HRID 1514859
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[NH4+:23].[OH-]>O1CCOCC1.O>[NH2:23][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21]

Komponenten

5

Edukt 2

HCID 14923Ammonium HydroxideHCID 47954984-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

Produkt 1

HCID 669661164-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a suspension of 4-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide (0.22 g) in dioxane (2 mL) was added NH4OH (3 mL). The reaction mixture was heated to 95° C. for 8 h. The mixture was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The extract was dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 hexane/EtOAc) afforded 4-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 3:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b777f18b188341a190f700d440237782
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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