p-Toluenesulfonic acid → HCID 18694867, compound

HRID 1871055Notes

Reaction equation

HRID 1871055 reaction equation
O1CCOCC1.[Cl:7][C:8]1[C:17]([C:18](=[O:25])[C:19](=[CH:21][N:22](C)C)[CH3:20])=[C:16]([Cl:26])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Cl.NO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[Cl:7][C:8]1[C:17]([C:18]2[O:25][N:22]=[CH:21][C:19]=2[CH3:20])=[C:16]([Cl:26])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 443297Hydroxyamine hydrochlorideHCID 54569527HCID 54569527, compound

Product 1

HCID 18694867HCID 18694867, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 30 ml dioxane and 16 ml water, was dissolved methyl 2,4-dichloro-3-(2-dimethylaminomethylidene-1-oxopropyl)benzoate in an amount of 7.57 g, and the resulting solution was then added with hydroxylamine hydrochloride in an amount of 1.70 g and further stirred for 17 hours at an ambient temperature. After distillating out the solvent in the solution under reduced pressure, the residue obtained was dissolved in ethyl acetate, and the solution was then washed with saturated saline solution and dried with anhydrous magnesium sulfate. After distillating out the solvent in the solution under reduced pressure, crude oxime-form of the product obtained was dissolved in 30 ml toluene and then stirred for 14.5 hours under reflux and heating following to the addition of p-toluenesulfonic acid in an amount of 0.5 g. The reacted-mixture was cooled, then washed with water and saturated saline solution in turn and dried with anhydrous magnesium sulfate. The solvent used for the mixture was then condensed under reduced pressure, and the residue obtained was purified by using a silica gel column chromatography to obtain an objective product, methyl 2,4-dichloro-3-(4-methylisoxazol-5-yl)benzoate in an amount of 0.83 g.

Workup

  1. customthe residue obtained
  2. washthe solution was then washed with saturated saline solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customobtained
  5. stirringstirred for 14.5 hours
  6. temperatureunder reflux
  7. temperatureheating
  8. temperatureThe reacted-mixture was cooled
  9. washwashed with water and saturated saline solution in turn
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customcondensed under reduced pressure
  12. customthe residue obtained
  13. customwas purified

Sources & evidence

ORD record
ord-2fd9dfa60a064d7f80fc08102691b881
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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