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

HRID 22295ノート

反応式

HRID 22295 の反応式
[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

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 53776389HCID 53776389、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cba0ad7915c74481bc045fbdecd92ebf
出典データセット
uspto-grants-1995_06
特許番号
US05428047

反応ノート

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