Pyridine → 2-[(2-Fluorophenyl)methyl]-4,4-dimethylisoxazolidine-3,5-dione

HRID 1155465ノート

反応式

HRID 1155465 の反応式
N1C=CC=CC=1.[CH3:7][C:8]([CH3:15])([C:12](Cl)=[O:13])[C:9](Cl)=[O:10].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][NH:24][OH:25]>C(Cl)Cl>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][N:24]1[C:9](=[O:10])[C:8]([CH3:15])([CH3:7])[C:12](=[O:13])[O:25]1

参加物

5

反応物 3

HCID 1049PyridineHCID 4523180Dimethylmalonyl DichlorideHCID 12811043N-[(2-Fluorophenyl)methyl]hydroxylamine2 回

生成物 1

HCID 128110502-[(2-Fluorophenyl)methyl]-4,4-dimethylisoxazolidine-3,5-dione収率 91.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-25 °C

実験手順

The procedure of Example III was utilized with 10.2 ml (0.128 mole) pyridine, 10.2 grams (0.060 mole) dimethylmalonyl chloride and 120 ml methylene chloride in solution under argon at -72° C., to which 8.5 grams (0.060 mole) of N-(2-fluorophenylmethyl)hydroxylamine (Intermediate F) in 25 ml methylene chloride was added in a single portion, raising the temperature immediately to -25° C., and stirring was continued at 0° C. for two hours. Gas chromatography on a sample of the reaction mixture showed only one major peak. The reaction mixture was washed with 2 N hydrochloric acid and water, the methylene chloride layer was separated and dried over sodium sulfate, and after removal of sodium sulfate by filtration, the solvent was removed under reduced pressure, leaving 13.0 grams of a yellow viscous liquid (91% yield). The nmr and ir spectra were consistent with the assigned structure.

後処理

  1. additionwas added in a single portion
  2. washThe reaction mixture was washed with 2 N hydrochloric acid and water
  3. customthe methylene chloride layer was separated
  4. dry with materialdried over sodium sulfate
  5. customafter removal of sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-6137d4825332482d92380d4b5c677f2e
出典データセット
uspto-grants-1981_11
特許番号
US04302238

反応ノート

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