Hydrochloric Acid → 2-(4-Chlorobenzyl)-2-(2-chloro-2-propenyl)malononitrile

HRID 749515

反応式

HRID 749515 の反応式
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]([C:10]#[N:11])[C:8]#[N:9])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:18][C:19]([CH2:21]Cl)=[CH2:20].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]([CH2:21][C:19]([Cl:18])=[CH2:20])([C:8]#[N:9])[C:10]#[N:11])=[CH:12][CH:13]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 65652,3-DichloropropeneHCID 180822-((4-Chlorophenyl)methyl)propanedinitrileHCID 24758Sodium hydrideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 222350252-(4-Chlorobenzyl)-2-(2-chloro-2-propenyl)malononitrile収率 27%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

First, 0.50 g of (4-chlorobenzyl)malononitrile was dissolved in 10 ml of N,N-dimethylformamide, to which 0.16 g of sodium hydride (60% in oil) was added under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 0.48 ml of 2,3-dichloropropene was added dropwise, followed by stirring at room temperature for 5 hours. Then, 10% hydrochloric acid was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.19 g of 2-(4-chlorobenzyl)-2-(2-chloro-2-propenyl)malononitrile (the present compound (1)).

後処理

  1. additionwas added under ice cooling
  2. stirringby stirring at room temperature for 5 hours
  3. extractionwas extracted with diethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6a4c1d8406c64858a00c58cb6370db78
出典データセット
uspto-grants-2008_07
特許番号
US07402691B2

関連ノート

読み込み中…