Sulfuryl chloride → HCID 178519003, compound

HRID 612941Notes

Reaction equation

HRID 612941 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([OH:13])[CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:17])(=O)=O>O1CCCC1.C1C=CC=CC=1>[Cl:17][C:9]1[C:10]([OH:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178515608HCID 178515608, compound

Product 1

HCID 178519003HCID 178519003, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 5-(4-chlorophenyl)-3-hydroxyisoxazole (50.0 g) in dry tetrahydrofuran (300 ml), a solution of sulfuryl chloride (34.5 g) in dry benzene (50 ml) was added dropwise with stirring at 5° C. The resulting mixture was stirred at the same temperature for 30 minutes and then at room temperature for one hour and further refluxed for 3 hours. The solvent of the reaction mixture was evaporated under reduced pressure, and the solid thus obtained was recrystallized from ethanol to obtain the title compound (44.2 g, 76.8%) as colorless needle-like crystals.

Workup

  1. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  2. temperaturefurther refluxed for 3 hours
  3. customThe solvent of the reaction mixture was evaporated under reduced pressure
  4. customthe solid thus obtained
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3e395e14c0d14739a93d12de03a0ea64
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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