Reaktion #80907

Reaktionsgleichung

pyridine

5-chloro-2nitrobenzonitrile

2-naphthalenethiol

potassium carbonate

→

2-nitro-5-(naphth-2-ylthio)benzonitrile

Ausbeute 80.1%

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   Temperaturto warm to ambient temperature
3. 3
   workup.STIRRINGwhere it was stirred for about 18 hours
4. 4
   Sonstigeformed
5. 5
   FiltrationThe solid was collected by filtration
6. 6
   Waschenwas washed in turn with an aqueous solution of 10% pyridine, water
7. 7
   workup.DISSOLUTIONThe solid was then dissolved in ethyl acetate
8. 8
   Trocknendried with magnesium sulfate
9. 9
   FiltrationThe mixture was filtered
10. 10
    Einengenthe filtrate was concentrated under reduced pressure to a residual solid
11. 11
    WaschenElution
12. 12
    Einengenconcentrated under reduced pressure

Vorschrift

A stirred solution of 10.0 grams (0.055 mole) of 5-chloro-2nitrobenzonitrile and 8.8 grams (0.055 mole) of 2-naphthalenethiol in 80 mL of N,N-dimethylformamide was cooled to 0° C., and 7.6 grams (0.055 mole) of potassium carbonate was added. Upon completion of addition, the reaction mixture was stirred at 0° C. for 1 hour. Thin layer chromatographic (TLC) analysis of the reaction mixture after this time indicated that the reaction had not gone to completion. The reaction mixture was then allowed to warm to ambient temperature, where it was stirred for about 18 hours. The reaction mixture was stirred with 80 mL of pyridine and then was diluted with water until a solid precipitate formed. The solid was collected by filtration and was washed in turn with an aqueous solution of 10% pyridine, water, an aqueous solution of 1% hydrochloric acid, and finally with water. The solid was then dissolved in ethyl acetate and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residual solid. The solid was subjected to column chromatography on silica gel. Elution was accomplished with 10% ethyl acetate in heptane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 13.5 grams of 2-nitro-5-(naphth-2-ylthio)benzonitrile. A small sample was recrystallized from ethyl acetate/hexane, mp 139°-140° C. The NMR spectrum was consistent with the proposed structure.

Quelle