Pyridine → 1-[2-(4-chloromethylphenyl)-2-oxo-ethyl]-4-(4-fluoro-benzyloxy)-1H-pyridin-2-one

HRID 564102

Reaktionsgleichung

Reaktionsgleichung von HRID 564102
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=3)=[O:16])[C:10](=[O:25])[CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:36])=O>C(Cl)Cl.O>[Cl:36][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][N:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][C:10]2=[O:25])=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 580428344-(4-Fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Produkt 1

HCID 580427031-[2-(4-chloromethylphenyl)-2-oxo-ethyl]-4-(4-fluoro-benzyloxy)-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 1.20 g (3.27 mmol) 4-(4-fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one (preparation 31.1) in 20 mL DCM is added 0.29 mL (3.59 mmol) pyridine and 0.26 mL (3.59 mmol) thionylchloride at 0° C. The reaction mixture is stirred 1 h at 0° C., is warmed to RT and is then diluted with water. The organic phase is washed with saturated aqueous KHSO4-solution and then with water, dried over MgSO4, filtered over charcoal and the solvent is evaporated.

Aufarbeitung

  1. temperatureis warmed to RT
  2. washThe organic phase is washed with saturated aqueous KHSO4-solution
  3. dry with materialwith water, dried over MgSO4
  4. filtrationfiltered over charcoal
  5. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e661e0376b52405a962b4a9660afb778
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

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