Thionyl Chloride → 5-Methyl-1,2-oxazole-4-carbonyl chloride

HRID 329780Notes

Reaction equation

HRID 329780 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[O:10][N:9]=[CH:8][C:7]=1[C:11]([OH:13])=O>CN(C)C=O>[CH3:5][C:6]1[O:10][N:9]=[CH:8][C:7]=1[C:11]([Cl:3])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14252405-Methylisoxazole-4-carboxylic acid

Product 1

HCID 27599175-Methyl-1,2-oxazole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (118 g) was added to 5-methylisoxazol-4-yl carboxylic acid (42 g) and stirred at room temperature as dimethylformamide (0.2 ml) was added. The solution was heated under reflux for 2 hours with stirring. Excess thionyl chloride was removed in vacuo at 50° C., then the residue was distilled through a 15 cm Vigreaux column at reduced pressure to give an oil, b.p. 32°-34° C./0.1 mm Hg.

Workup

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 2 hours
  4. customExcess thionyl chloride was removed in vacuo at 50° C.
  5. distillationthe residue was distilled through a 15 cm Vigreaux column at reduced pressure
  6. customto give an oil, b.p. 32°-34° C./0.1 mm Hg

Sources & evidence

ORD record
ord-cbe1f7e242b14178823365435748f647
Source dataset
uspto-grants-1990_01
Patent number
US04892963

Reaction notes

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