2,6-Dichlorobenzaldchloroxime → 2,2-dichloro-N-[4-[3-(2,6-dichlorophenyl)-5-isoxazolyl]phenyl]acetamide

HRID 2053384ノート

反応式

HRID 2053384 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9](Cl)=[N:10][OH:11].[Cl:13][CH:14]([Cl:26])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1)=[O:16]>C1COCC1.C(N(CC)CC)C>[Cl:13][CH:14]([Cl:26])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:11][N:10]=[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[CH:25]=2)=[CH:20][CH:19]=1)=[O:16]

参加物

5

反応物 2

HCID 28001642,6-DichlorobenzaldchloroximeHCID 211003382,2-Dichloro-N-(4-ethynylphenyl)Acetamide2 回

生成物 1

HCID 103418252,2-dichloro-N-[4-[3-(2,6-dichlorophenyl)-5-isoxazolyl]phenyl]acetamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

2,6-Dichloro-N-hydroxybenzenecarboximidoyl chloride (1.01 g, 4.5 mmol) and 2,2-dichloro-N-(4-ethynylphenyl)acetamide (1.01 g, 4.42 mmol) were dissolved in anhydrous THF (40 mL) and triethylamine (1.0 mL). The mixture was stirred at room temperature for 1 h then heated at reflux for 4 h to generate the 2,6-dichlorophenyl nitrile oxide intermediate, which reacted by a 1,3-dipolar cycloaddition reaction with 2,2-dichloro-N-(4-ethynylphenyl)acetamide. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was purified by column chromatography on silica gel, eluting with 8:2 hexanes-ethyl acetate. The appropriate fractions were combined to give 2,2-dichloro-N-[4-[3-(2,6-dichlorophenyl)-5-isoxazolyl]phenyl]acetamide as a tan solid.

後処理

  1. temperaturethen heated
  2. temperatureat reflux for 4 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was purified by column chromatography on silica gel
  10. washeluting with 8:2 hexanes-ethyl acetate

出典と根拠

ORDレコード
ord-3bbe3440a869427abfbc58814e52f4a4
出典データセット
uspto-grants-2008_02
特許番号
US07326790B2

反応ノート

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