Thionyl Chloride → HCID 66647314, compound

HRID 1923499Notes

Reaction equation

HRID 1923499 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:17][CH2:13][C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:5][O:6][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66643722(5-Methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol

Product 1

HCID 66647314HCID 66647314, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (3.0 g, 16 mmol) in DCM (30 mL) at 0° C. was added thionyl chloride (3.75 g, 32 mmol) and the resulting mixture stirred for 1 h and then evaporated. After 1 h the reaction mixture was quenched with a solution of sodium hydrogen carbonate (1N, 15 mL) and extracted with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, filtered and concentrated to give the title compound (3.2 g, 96%) as a light brown solid. MS: m/e=209.1 [M+H]+.

Workup

  1. customevaporated
  2. customAfter 1 h the reaction mixture was quenched with a solution of sodium hydrogen carbonate (1N, 15 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-091f90d1c14a405389fb1d40ae3aa52a
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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