Thionyl Chloride → 5-Methyl-3-phenylisoxazole-4-carbonyl chloride

HRID 463785

Reaction equation

HRID 463785 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13](C(O)=O)=[O:14].S(Cl)([Cl:20])=O>N1C=CC=CC=1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([Cl:20])=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202651525-Methyl-3-phenyl-4-isoxazoloyl carboxylic acid

Product 1

HCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A mixture of 111.76 g of 5-methyl-3-phenyl-4-isoxazoloyl carboxylic acid, 6 drops of pyridine and 29.5 ml of thionyl chloride is stirred under reflux for 4 hrs. The excess thionyl chloride is evaporated in vacuo. Distillation of the residue yields 113.74 g of yellow liquid.

Workup

  1. temperatureunder reflux for 4 hrs
  2. customThe excess thionyl chloride is evaporated in vacuo
  3. distillationDistillation of the residue

Sources & evidence

ORD record
ord-e5e56676ef5d48e9b65a67a4cd85f5d8
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Linked notes

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