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2,8-Dibromo-3,7-dinitrodibenzothiophene-5-oxide → Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxide

HRID 376731
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 376731
[Br:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[S:6](=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.BrC1C([N+]([O-])=O)=CC2S(=[O:36])C3C=CC(Br)=CC=3C=2C=1.I([O-])(=O)(=O)=O.[Na+]>[Ru](Cl)(Cl)Cl.O.O1CCCC1.C(#N)C.O1CCOCC1.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[S:6](=[O:36])(=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1
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Komponenten

10

Edukt 3

HCID 158859092,8-Dibromo-3,7-dinitrodibenzothiophene-5-oxideHCID 158859102,8-Dibromo-3-nitrodibenzothiophene-5-oxideHCID 23667635Sodium periodate

Produkt 1

HCID 4571975Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 61850Ruthenium trichloride
Katalysator
HCID 962WaterLösungsmittel3×
HCID 5943Carbon TetrachlorideLösungsmittel
HCID 6342AcetonitrileLösungsmittel2×
HCID 8028TetrahydrofuranLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Referring to Scheme II, a mixture of 2,8-dibromo-3,7-dinitrodibenzothiophene-5-oxide 3a and 2,8-dibromo-3-nitrodibenzothiophene-5-oxide 3b was treated in a heterogeneous solvent mixture which include but not limited to acetonitrile, carbon tetrachloride and water, p-dioxane and water, acetonitrile, tetrahydrofuran and water; with an oxidizing agent which include but not limited to sodium periodate and ruthenium(III) chloride; stirred at a temperature range from 15-75° C. until completion as indicated by TLC to yield 2,8-dibromo-3,7-dinitrodibenzothiophene-5,5-dioxide 9 as the isolated product. Treating 2,8-dibromo-3,7-dinitrodibenzothiophen-5,5-dioxide 9 with a reducing agent which include but are not limited to powdered iron, tin (II) chloride, zinc metal or palladium on charcoal with hydrogen in alcoholic solvents which include but are not limited to methyl alcohol, ethyl alcohol, propyl alcohol or 2-methoxy-ethanol and the like; and an organic acid which includes but is not limited to acetic acid; at a temperature range from 50-120° C. for about 2 hours or until completion to give 2,8-dibromo-5,5-dioxo-5H-5λ6 -dibenzothiophene-3,7-diamine 10.

Aufarbeitung

  1. additionwas treated in a heterogeneous solvent mixture which

Quellen und Nachweise

ORD-Eintrag
ord-15bd87a547b04673893d78ec055368d6
Quelldatensatz
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06022307

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