Thionyl Chloride → (E)-2,6-difluorocinnamoyl chloride

HRID 50887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50887
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1/[CH:4]=[CH:5]/[C:6](O)=[O:7].S(Cl)([Cl:16])=O>C1C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1/[CH:4]=[CH:5]/[C:6]([Cl:16])=[O:7]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 53722672,6-Difluorocinnamic acid

Produkt 1

HCID 11424232(E)-2,6-difluorocinnamoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (E)-2,6-difluorocinnamic acid (331 mg, 1.8 mmol) in benzene (10 ml) was added thionyl chloride (0.5 ml) and the mixture was heated to reflux for 60 min. Volatiles were removed by evaporation to give crude (E)-2,6-difluorocinnamoyl chloride. Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine (250 mg, 1.4 mmol) and (E)-2,6-difluorocinnamoyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate/ethanol yielded the titled compound. MW: 369.80; mp: 204.5-206.5° C.; 1H-NMR (DMSO) δ: 8.82-8.77 (1H, m), 8.29-8.18 (1H, m), 8.00 (1H, d, J=16.5 Hz), 7.89-7.80 (2H, m), 7.74-7.66 (1H, m), 7.58-7.34 (4H, m), 7.39 (1H, d, J=16.5 Hz), 7.27-7.16 (2H, m).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 60 min
  3. customVolatiles were removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-b76fc3aba48e4d5ebc30059fd3fa54fe
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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