Water → HCID 86611704, compound

HRID 424649Notes

Reaction equation

HRID 424649 reaction equation
[OH2:1].Br[CH2:3][C:4]1[C:12]2[C:7](=[N:8][C:9]([Cl:13])=[CH:10][CH:11]=2)[S:6][N:5]=1>CS(C)=O>[Cl:13][C:9]1[N:8]=[C:7]2[S:6][N:5]=[C:4]([CH2:3][OH:1])[C:12]2=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86611703HCID 86611703, compound

Product 1

HCID 86611704HCID 86611704, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Water (8 mL) was added to a solution of 3-(bromomethyl)-6-chloroisothiazolo[5,4-b]pyridine (19.0 mmol) in dimethylsulfoxide (40 mL) and the reaction mixture was heated at 80° C. for 1.5 h. The reaction mixture was then quenched with water (50 mL) and the resulting solution was extracted with ethyl acetate (3×40 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to provide the crude (6-chloroisothiazolo[5,4-b]pyridin-3-yl) methanol as a yellow solid.

Workup

  1. customThe reaction mixture was then quenched with water (50 mL)
  2. extractionthe resulting solution was extracted with ethyl acetate (3×40 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8ace23114ed45648083a50a0e6f3842
Source dataset
uspto-grants-2012_01
Patent number
US08106066B2

Reaction notes

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