Thionyl Chloride → HCID 22930764, compound

HRID 349971Notes

Reaction equation

HRID 349971 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:17]=[C:16]([CH2:18]O)[O:15][N:14]=1.S(Cl)([Cl:22])=O>>[Cl:22][CH2:18][C:16]1[O:15][N:14]=[C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:17]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22930681HCID 22930681, compound

Product 1

HCID 22930764HCID 22930764, compoundYield 98%

Procedure

A mixture of 3-(2-quinolylmethoxy)-5-isoxazolylmethanol (1.54 g) and thionyl chloride (5 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 to obtain 2-(5-chloromethyl-3-isoxazolyloxymethyl)quinoline (1.61 g, yield 98%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 126–127° C.

Workup

  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

Sources & evidence

ORD record
ord-00b0d5f3fae747b6995206cb42b91029
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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