Dimethyl Sulfoxide → HCID 66702998, compound

HRID 424643Notes

Reaction equation

HRID 424643 reaction equation
Br[CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[S:5][N:4]=1.CS(C)=[O:14]>O>[S:5]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:11]2[C:3]([CH2:2][OH:14])=[N:4]1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 667026993-(Bromomethyl)isothiazolo[5,4-b]pyridine

Product 1

HCID 66702998HCID 66702998, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of the crude 3-(bromomethyl)isothiazolo[5,4-b]pyridine (3.49 mmol) in dimethylsulfoxide (20 mL) was treated with water (4 mL) and the reaction mixture was heated at 80° C. for 1.5 h. The reaction mixture was diluted with water (100 mL), filtered through Celite, and was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with water, dried (magnesium sulfate), and concentrated to provide isothiazolo[5,4-b]pyridin-3-ylmethanol in 31% yield as yellow oil.

Workup

  1. filtrationfiltered through Celite
  2. extractionwas extracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-353f1cbd6e90492aacd05c1c0054f38d
Source dataset
uspto-grants-2012_01
Patent number
US08106066B2

Reaction notes

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