Hydrochloric Acid → Dapsone

HRID 492279

Reaktionsgleichung

Reaktionsgleichung von HRID 492279
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].Cl>[Pd].O.CO>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH:18]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 747624-((4-Nitrophenyl)sulfonyl)benzenamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 2955DapsoneAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

In a hydrogenation vessel 4-(4′-Nitro-benzenesulfonyl)-phenylamine (100 g), p-toluensulfonic acid (68.4 g), methanol (350 ml), water (150 ml) and 10% palladium on charcoal (7.6 g) are charge. The mixture is allowed to react with hydrogen at approximately 50° C. and 5 bar pressure. At reaction completion, hydrochloric acid is added, the catalyst is filtered and dried. 82 g of crude Dapsone are obtained (82% yield; >99.5% purity).

Aufarbeitung

  1. additionis added
  2. filtrationthe catalyst is filtered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5cfbd91163c64d64bab51b68c7074138
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531694B2

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