5-Methyl-3-phenylisoxazole-4-carboxylic acid → 5-Methyl-3-phenylisoxazole-4-carbonyl chloride

HRID 2199531Notes

Reaction equation

HRID 2199531 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]([OH:15])=O.S(Cl)([Cl:18])=O>>[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:18])=[O:15]

Participants

3

Reactant 2

HCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chlorideYield 93%

Procedure

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (1.0 g, 4.9 mmol, commercially available) and thionyl chloride (5 ml) was heated under reflux for 3 h. Removal of excess volatiles by evaporation afforded 5-methyl-3-phenyl-isoxazole-4-carbonyl chloride (1.01 g, 93%) as a yellow oil, which was used without further purification in the next reaction.

Workup

  1. temperatureunder reflux for 3 h
  2. customRemoval of excess volatiles
  3. customby evaporation

Sources & evidence

ORD record
ord-1d2b112c089c4c7083ad7b8abb33e3d8
Source dataset
uspto-grants-2016_06
Patent number
US09359310B2

Reaction notes

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