Thionyl Chloride → 4-Ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride

HRID 1411143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1411143
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:6](=[O:17])[C:5]=1[C:18]([OH:20])=O)[CH3:2].O=S(Cl)[Cl:23]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:6](=[O:17])[C:5]=1[C:18]([Cl:23])=[O:20])[CH3:2]

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 585350974-Ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Produkt 1

HCID 866675054-Ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of Example B1 (35 g, 126 mmol) in toluene (400 mL) was treated with SOCl2 (120 g, 1.01 mol) and one drop of DMF, and was heated to reflux for 2 h. The mixture was concentrated in vacuo to afford 4-ethoxy-1-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl chloride (33.5 g, 100% yield). The residue was carried into the next reaction without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationThe mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d271e5b63834925924ab1bd9442aa74
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921565B2

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