Thionyl Chloride → 3-(4-Methylphenyl)isoxazole-5-carboxylic acid chloride

HRID 1742533Notes

Reaction equation

HRID 1742533 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:16]=[C:15]([C:17]([OH:19])=O)[O:14][N:13]=2)=[CH:8][CH:7]=1>CN(C)C=O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:16]=[C:15]([C:17]([Cl:3])=[O:19])[O:14][N:13]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 199769083-(4-Methylphenyl)-1,2-oxazole-5-carboxylic acid

Product 1

HCID 537159153-(4-Methylphenyl)isoxazole-5-carboxylic acid chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 40 ml of thionyl chloride, 7.3 g (35.9 mmol) of 3-(4-methylphenyl)isoxazole-5-carboxylic acid obtained above in the procedure (2) were refluxed for 4 hours in the presence of 0.1 ml of dimethylformamide. Thionyl chloride was distilled off under reduced pressure, followed by the addition of 100 ml of benzene. The resultant mixture was distilled under reduced pressure so that 3-(4-methylphenyl)isoxazole-5-carboxylic acid chloride was obtained as a solid. The solid was provided for the next step without purification.

Workup

  1. customobtained above in the procedure (2)
  2. distillationThionyl chloride was distilled off under reduced pressure
  3. additionfollowed by the addition of 100 ml of benzene
  4. distillationThe resultant mixture was distilled under reduced pressure so that 3-(4-methylphenyl)isoxazole-5-carboxylic acid chloride
  5. customwas obtained as a solid
  6. customThe solid was provided for the next step without purification

Sources & evidence

ORD record
ord-30eb2d4db01a43bbb13544e8c5fece1e
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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