Dimethylformamide → 3,7-Diaminodibenzothiophene-5,5-dioxide

HRID 1089178

Reaktionsgleichung

Reaktionsgleichung von HRID 1089178
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][C:14]([N+:16]([O-])=O)=[CH:15][C:10]=3[S:9](=[O:20])(=[O:19])[C:8]=2[CH:21]=1)([O-])=O.CN(C)C=O.[H][H]>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:10]=3[S:9](=[O:20])(=[O:19])[C:8]=2[CH:21]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 17124133,7-Dinitrodibenzo[b,d]thiophene 5,5-dioxideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 804123,7-Diaminodibenzothiophene-5,5-dioxideAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 10.0 g of 3,7-dinitrodibenzothiophene S,S-dioxide, 180 ml of dimethylformamide, 20 ml of glacial acetic acid and 1.0 g of 5% palladium on carbon was hydrogenated in a Parr apparatus until hydrogen uptake ceased. The mixture was then filtered through diatomaceous earth, the filtrate poured into 1 liter of ice water, the solid collected by filtration, washed with ethanol and ether and dried at 110° C., giving 7.86 g of the desired product as a solid mp 320°-330° C.(dec.).

Aufarbeitung

  1. filtrationThe mixture was then filtered through diatomaceous earth
  2. additionthe filtrate poured into 1 liter of ice water
  3. filtrationthe solid collected by filtration
  4. washwashed with ethanol and ether
  5. customdried at 110° C.

Quellen und Nachweise

ORD-Eintrag
ord-974e591d85bf47d1b5cb4a543f4cbb99
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04965284

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