Cesium carbonate → 3-(3-Nitrophenylthio)pyridine

HRID 710607

Reaktionsgleichung

Reaktionsgleichung von HRID 710607
[N+:1]([C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.O=C1CCCCC1C(OCC)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu](I)I>[N+:1]([C:4]1[CH:5]=[C:6]([S:10][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 2435763-Nitrobenzene-1-thiol

Produkt 1

HCID 1184923323-(3-Nitrophenylthio)pyridineAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

3-nitrophenylmercaptan (5 g, 32 mmol), 3-bromopyridine (6.1 g, 38.6 mmol), ethyl 2-oxocyclohexylformate (1.1 g, 6.5 mmol), copper iodide (608 mg, 4.2 mmol), cesium carbonate (2.3 g, 70.6 mmol) were dissolved in 500 ml of DMSO, reacted under microwaves at 100° C. for 8 h. After being extracted with water and DCM, the organic phase was dried and separated with column chromatography to obtain an object product 3.2 g.

Aufarbeitung

  1. customreacted under microwaves at 100° C. for 8 h
  2. extractionAfter being extracted with water and DCM
  3. customthe organic phase was dried
  4. customseparated with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a0d13f15a77e4ef9bae4bf6373c2ca64
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181244B1

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