2-Aminobenzonitrile → diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate

HRID 54898

反応式

HRID 54898 の反応式
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:10]([O:12][P:13]([CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O:15][CH2:16][CH3:17])=[O:14])[CH3:11]>N1C=CC=CC=1.ClCCl>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:23]([C:22]1[CH:26]=[CH:27][C:19]([CH2:18][P:13](=[O:14])([O:12][CH2:10][CH3:11])[O:15][CH2:16][CH3:17])=[CH:20][CH:21]=1)=[O:24])#[N:9]

参加物

5

反応物 2

HCID 729132-AminobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

生成物 1

HCID 10738021diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzylphosphonate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A 15.7 g portion of anthranilonitrile was dissolved in 50 ml of pyridine. While the solution was stirred under ice-cooling, a solution of 40.7 g of 4-[(diethoxyphosphoryl)-methyl]benzoyl chloride in 50 ml of dry dichloromethane was added dropwise. The stirring was continued at room temperature for 12 hours, after which the reaction mixture was diluted with 200 ml of dichloromethane and washed with diluted hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform-n-hexane to provide 25.9 g of diethyl 4-[N-(2-cyanophenyl)carbamoyl]benzyl-phosphonate as colorless crystals.

後処理

  1. temperaturecooling
  2. washwashed with diluted hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from chloroform-n-hexane

出典と根拠

ORDレコード
ord-607114bdcd884d68b566960c08712939
出典データセット
uspto-grants-1997_04
特許番号
US05624918

関連ノート

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