Water → HCID 15227586, compound

HRID 1109513Notes

Reaction equation

HRID 1109513 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][N:14]=[C:13]([O:16][CH2:17][CH:18]3[O:20][CH2:19]3)[C:12]=2[CH:21]=1.O>C(#N)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][N:14]=[C:13]([O:16][CH2:17][CH:18]([OH:20])[CH2:19][OH:2])[C:12]=2[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15227585HCID 15227585, compound

Product 1

HCID 15227586HCID 15227586, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

256 ml of a 10% w/v aqueous solution of potassium carbonate were added to a suspension of 21.0 g (92.7 mmoles) of 5-chloro-3-(2,3-epoxypropoxy)-1,2-benzisoxazole (prepared according to the method described in Japanese Patent Provisional Publication No. Sho. 52-31070) in 100 ml of acetonitrile, and the mixture was then heated under reflux for 3 hours. At the end of this time, the reaction mixture was cooled by allowing it to stand, and then 500 ml of water were added. The reaction mixture was then extracted with 1 liter of ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the solvent was removed by distillation to give a solid residue. This was then recrystallized from a mixture of ethyl acetate and diethyl ether, to give 16.7 g (yield 74.2%) of the title compound as a colorless amorphous powder, melting at 61°-62° C.

Workup

  1. customprepared
  2. temperatureunder reflux for 3 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. extractionThe reaction mixture was then extracted with 1 liter of ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customthe desiccant was removed by filtration
  8. customthe solvent was removed by distillation
  9. customto give a solid residue
  10. customThis was then recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-93e804f62b1b4736b35e1c0cbf41ae6d
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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