Sodium Chloride → HCID 19020727, compound

HRID 1109515Notes

Reaction equation

HRID 1109515 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[O:18][N:17]=[C:16]([O:19][CH2:20][CH:21]3[O:23][CH2:22]3)[CH:15]=2)[CH:11]=[CH:12][CH:13]=1.[Cl-].[Na+]>C(#N)C>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[O:18][N:17]=[C:16]([O:19][CH2:20][CH:21]([OH:23])[CH2:22][OH:2])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 19020732HCID 19020732, compound

Product 1

HCID 19020727HCID 19020727, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 ml (72.3 mmoles) of a 10% w/v aqueous solution of potassium carbonate were added to a solution of 15.0 g (59.6 mmoles) of 5-(m-chlorophenyl)-3-(2,3-epoxypropoxy)isoxazole (prepared as described in Preparation 2) in 50 ml of acetonitrile, and the mixture was heated under reflux for 3 hours. At the end of this time, the reaction mixture was cooled by allowing it to stand, and then 400 ml of a 10% w/v aqueous solution of sodium chloride were added thereto, and the mixture was extracted twice, each time with 400 ml of ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was then purified by column chromatography through silica gel, eluted with a 1:2 by volume mixture of benzene and ethyl acetate, to give 13.2 g (yield 82.5%) of the title compound as a colorless amorphous powder, melting at 92°-93° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. extractionthe mixture was extracted twice
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was then purified by column chromatography through silica gel
  8. washeluted with a 1:2 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-1c85718544cd44d8b8ce0467162f0c8a
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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