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

HRID 1295238Notes

Reaction equation

HRID 1295238 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:6][C:2]=2[CH3:1])=[N:20][CH:19]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 229306846-(5-Methyl-2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol

Product 1

HCID 229307085-Chloromethyl-2-(5-methyl-2-phenyl-4-thiazolylmethoxy)pyridineYield 92%

Procedure

A mixture of 6-(5-methyl-2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol (1.56 g) and thionyl chloride (10 ml) was stirred at room temperature for 1 hr. The mixture was concentrated under reduced pressure and ice water was added to the residue. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 5-chloromethyl-2-(5-methyl-2-phenyl-4-thiazolylmethoxy)pyridine (1.53 g, yield 92%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 78–79° C.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ice water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2b8760ba44554eb1ad83627da63e6b6d
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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