Reaktion #63566

Reaktionsgleichung

3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio)-nitrobenzene

→

3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) aniline

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   Filtrationfiltered
3. 3
   Sonstigeevaporated to dryness
4. 4
   workup.DISSOLUTIONthe resulting gum redissolved in chloroform
5. 5
   Waschenwashed with water (twice),
6. 6
   Trocknendried over anhydrous magnesium sulphate
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto give the crude product as a light brown gum (27.17 g)
9. 9
   SonstigeThis gum was chromatographed on silica gel
10. 10
    Sonstigeethyl acetate-petroleum spirit (60°-80°, gradient elution)

Vorschrift

3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio)-nitrobenzene (28.60 g) and iron powder (35 g) were stirred with heating in glacial acetic acid (250 ml) at 90° for 40 minutes. The mixture was cooled, filtered, then evaporated to dryness and the resulting gum redissolved in chloroform, washed with water (twice), dried over anhydrous magnesium sulphate and evaporated to give the crude product as a light brown gum (27.17 g). This gum was chromatographed on silica gel using ethyl acetate-petroleum spirit (60°-80°, gradient elution) as eluant. 3,5-Dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)phenylthio) aniline was isolated as a pale yellow solid (21.29 g, 79%), m.p. 114°-115°.

Quelle