Thionyl Chloride → HCID 23024939, compound

HRID 349965Notes

Reaction equation

HRID 349965 reaction equation
[Cl:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[C:17]([CH2:19]O)[CH:16]=[CH:15][N:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>>[Cl:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[C:17]([CH2:19][Cl:23])[CH:16]=[CH:15][N:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 17930185HCID 17930185, compound

Product 1

HCID 23024939HCID 23024939, compoundYield 85%

Procedure

A mixture of 2-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)-4-pyridylmethanol (2.90 g) and thionyl chloride (10 ml) was stirred at room temperature for 1 hour. After the reaction mixture was concentrated, 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-chloro-2-(4-chloromethyl-2-pyridyloxymethyl)imidazo[1,2-a]pyridine (2.63 g, yield 85%) as colorless crystals from the fraction eluted with tetrahydrofuran. This was recrystallized from tetrahydrofuran-hexane. Melting point: 118–119° C.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate solution was 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

Sources & evidence

ORD record
ord-af5eece5d4e441ea96c14019a8ea1ea2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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