Carbon Tetrachloride → 5-Chloro-2-methoxy-3-pyridinecarbonyl chloride

HRID 1657580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657580
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(Cl)(Cl)[Cl:14].S(Cl)(Cl)=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]

Komponenten

5

Edukt 3

HCID 5943Carbon TetrachlorideHCID 24386Thionyl ChlorideHCID 98369735-Chloro-2-methoxynicotinic acid

Produkt 1

HCID 201566105-Chloro-2-methoxy-3-pyridinecarbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a suspension of 3.76 g. (0.02 mole) of 5-chloro-2-methoxynicotinic acid in 100 ml. of carbon tetrachloride, there were added 100 ml. of thionyl chloride in one portion and the resulting mixture was then refluxed on a steam bath for a period of 90 minutes. Upon completion of this step, the clear solution so obtained was cooled and then concentrated in vacuo at room temperature to afford a residual oil. The excess thionyl chloride present was next removed in the same manner as described in Preparation A for the production of 2-methoxynicotinoyl chloride, except that only 100 ml. of benzene was employed this time (i.e., during each purification step). The yield of pure 5-chloro-2-methoxynicotinoyl chloride, obtained as the residual product, was quantitative in this particular instance.

Aufarbeitung

  1. additionTo a suspension of 3.76 g
  2. customUpon completion of this step, the clear solution so obtained
  3. temperaturewas cooled
  4. concentrationconcentrated in vacuo at room temperature
  5. customto afford a residual oil
  6. customThe excess thionyl chloride present was next removed in the same manner
  7. customas described in Preparation A for the production of 2-methoxynicotinoyl chloride, except that only 100 ml
  8. customduring each purification step)

Quellen und Nachweise

ORD-Eintrag
ord-da49a25e91114e4d8907dd163c963add
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03961065

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