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Triethylamine → Methyl 3-dimethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate

HRID 255952
ノート
印刷プレビュー

反応式

HRID 255952 の反応式
[CH3:1][N:2]([CH3:9])[CH:3]=[CH:4][C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[C:24]([F:28])=[CH:23][C:19]=1[C:20](Cl)=[O:21]>O1CCOCC1>[CH3:1][N:2]([CH3:9])[CH:3]=[C:4]([C:20](=[O:21])[C:19]1[CH:23]=[C:24]([F:28])[C:25]([Cl:27])=[CH:26][C:18]=1[Cl:17])[C:5]([O:7][CH3:8])=[O:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 566587Methyl 3-(dimethylamino)acrylateHCID 27368212,4-Dichloro-5-fluorobenzoyl chloride

生成物 1

HCID 54215864Methyl 3-dimethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate収率 89.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

First a solution of 12.9 g of methyl 3-dimethylaminoacrylate in 25 ml of dioxane is added dropwise, and then 10.5 g of triethylamine are added to a solution of 22.75 g of 2,4-dichloro-5-fluorobenzoyl chloride in 80 ml of anhydrous dioxane, while cooling in ice and stirring. The mixture is stirred at room temperature for 3 hours, heated at 50°-60° C. for 1 hour, and the solvent is removed by distillation in vacuo and the residue is taken up in methylene chloride/H2O. The phases are separated, and the aqueous solution is again extracted with methylene chloride. The combined organic phases are washed with water, dried with sodium sulphate, and the methylene chloride is removed in vacuo. The crystalline residue is recrystallized from methanol/water. 28.5 g of methyl 3-dimethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate of melting point 107°-109° C. are obtained.

後処理

  1. temperaturewhile cooling in ice
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. temperatureheated at 50°-60° C. for 1 hour
  4. customthe solvent is removed by distillation in vacuo
  5. customThe phases are separated
  6. extractionthe aqueous solution is again extracted with methylene chloride
  7. washThe combined organic phases are washed with water
  8. dry with materialdried with sodium sulphate
  9. customthe methylene chloride is removed in vacuo
  10. customThe crystalline residue is recrystallized from methanol/water

出典と根拠

ORDレコード
ord-4f072d9b2f4943c599348ab0bb92c1e2
出典データセット
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04699992

反応ノート

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