Thionyl Chloride → HCID 22930783, Verbindung

HRID 349977

Reaktionsgleichung

Reaktionsgleichung von HRID 349977
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[N:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])=O>>[Cl:24][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]2[N:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[S:8][CH:9]=2)=[N:19][CH:18]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 229307412-(2-Phenyl-4-thiazolylmethoxy)-5-pyridylmethanol

Produkt 1

HCID 22930783HCID 22930783, VerbindungAusbeute 76 %

Versuchsvorschrift

A mixture of 6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol (2.98 g) and thionyl chloride (15 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain 5-chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine (2.40 g, yield 76%) as colorless crystals from the fraction eluted with ethyl acetate. This was recrystallized from tetrahydrofuran-hexane. Melting point: 117–118° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution
  2. additionwas added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-246dea5476394e2fb4a32963b4c8066e
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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