Thionyl Chloride → HCID 22930764, compound

HRID 1295235Notes

Reaction equation

HRID 1295235 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 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 to give 2-(5-chloromethyl-3-isoxazolyloxymethyl)quinoline (1.61 g, yield 98%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 126–127° 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-d16e918c31d4443cb6d835221eb04d1f
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

Loading…