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

HRID 1295237

Reaction equation

HRID 1295237 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6f58bfa0c4e14e6794e161c66fccea0a
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Linked notes

Loading…