Acetic Anhydride → 3-(3-Chloro-2-methyl-phenoxymethyl)-5-methyl-1,2,4-oxadiazole

HRID 22295Notes

Reaction equation

HRID 22295 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][C:7](=[N:9][OH:10])[NH2:8].[C:15]([O-])(=O)[CH3:16].[Na+].C(OC(=O)C)(=O)C>COCCOCCOC>[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][C:7]1[N:8]=[C:15]([CH3:16])[O:10][N:9]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 53776389HCID 53776389, compound

Product 1

HCID 199286483-(3-Chloro-2-methyl-phenoxymethyl)-5-methyl-1,2,4-oxadiazoleYield 56.6%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

7.0 g (32.6 mmol) of 3-chloro-2-methyl-phenoxy-acetamide oxime and 14.0 g (142.8 mmol) of sodium acetate are introduced into 80 ml of diglyme and the mixture is treated with 8.6 g (84.2 mmol) of acetic anhydride. The reaction mixture is stirred at reflux temperature until the reaction is complete (approximately 2 hours). The entire batch is subsequently concentrated, the product is treated with water, and the mixture is extracted using ethyl acetate. After the solvent has been distilled off, the crude product which remains is chromatographed over a silica gel column (silica gel 60 Merck, particle size: 0.040 to 0.063 mm) using methylene chloride as the eluent. 4.4 g (56.5% of theory) of 3-(3-chloro-2-methyl-phenoxymethyl)-5-methyl-1,2,4-oxadiazole are obtained.

Workup

  1. temperatureat reflux temperature until the reaction
  2. custom(approximately 2 hours)
  3. concentrationThe entire batch is subsequently concentrated
  4. additionthe product is treated with water
  5. extractionthe mixture is extracted
  6. distillationAfter the solvent has been distilled off
  7. customthe crude product which remains is chromatographed over a silica gel column (silica gel 60 Merck, particle size: 0.040 to 0.063 mm)

Sources & evidence

ORD record
ord-cba0ad7915c74481bc045fbdecd92ebf
Source dataset
uspto-grants-1995_06
Patent number
US05428047

Reaction notes

Loading…