Thionyl Chloride → 3-Phenylisoxazole-5-carbonyl chloride

HRID 1440327Notes

Reaction equation

HRID 1440327 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C:11]2[CH:15]=[C:14]([C:16]([OH:18])=O)[O:13][N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C)C=O>[C:5]1([C:11]2[CH:15]=[C:14]([C:16]([Cl:3])=[O:18])[O:13][N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 7374743-Phenylisoxazole-5-carboxylic Acid

Product 1

HCID 143973243-Phenylisoxazole-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Added to 500 g (4.2 mol) of thionyl chloride were 110 g (0.58 mol) of 3-phenylisoxazole-5-carboxylic acid prepared above in the procedure (2), followed by the further addition of 2 ml of dimethylformamide. The resulting mixture was heated under reflux for 3 hours. After completion of the reaction, thionyl chloride was distilled off under reduced pressure, followed by the addition of 500 ml of benzene. When the mixture thus obtained was distilled under reduced pressure, the title compound, i.e., 3-phenylisoxazole-5-carboxylic acid chloride was obtained as a solid. It was provided for the next step without purification.

Workup

  1. customprepared above in the procedure (2)
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 3 hours
  4. distillationwas distilled off under reduced pressure
  5. additionfollowed by the addition of 500 ml of benzene
  6. customWhen the mixture thus obtained
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-61104968dbd645a0bdcc41a461a628b0
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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