Hexane → 3-Nitro-2-(2-phenylsulfanyl-ethylsulfanyl)pyridine

HRID 888260

Reaktionsgleichung

Reaktionsgleichung von HRID 888260
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[SH:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.CCCCCC>CN(C=O)C>[N+:24]([C:23]1[C:18]([S:17][CH2:2][CH2:3][S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:19][CH:20]=[CH:21][CH:22]=1)([O-:26])=[O:25]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 21702((2-Chloroethyl)thio)benzeneHCID 178526679HCID 178526679, Verbindung

Produkt 1

HCID 671342393-Nitro-2-(2-phenylsulfanyl-ethylsulfanyl)pyridineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3.44 g (20.0 mmol) (2-chloroethyl)(phenyl)sulfane and 5.53 g (40.0 mmol) potassium carbonate were added to a solution of 1.56 g (10.0 mmol) 2-mercapto-3-nitropyridine in DMF (30 ml) and heated for 4 h at 60° C. Then the mixture was diluted with EE and washed with brine. The organic phase was separated off, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 9:1) of the residue yielded 1.93 g (6.6 mmol, 66%) 3-nitro-2-(2-phenylsulfanyl-ethylsulfanyl)pyridine.

Aufarbeitung

  1. additionThen the mixture was diluted with EE
  2. washwashed with brine
  3. customThe organic phase was separated off
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d3e7cedc03e24bf9af5227f9c7d87216
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247573B2

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