Thionyl Chloride → 5-Chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine

HRID 1295237

Reaktionsgleichung

Reaktionsgleichung von HRID 1295237
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][N: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:18]=[CH:19][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:15][CH:16]=1

Komponenten

3

Edukt 2

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

Produkt 1

HCID 229307835-Chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridineAusbeute 76 %

Versuchsvorschrift

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

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogen carbonate
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6f58bfa0c4e14e6794e161c66fccea0a
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241785B2

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