N,N-Diethylaniline → 1,1,2-Ethenetricarbonitrile, 2-(4-(diethylamino)phenyl)-

HRID 356226

反応式

HRID 356226 の反応式
[CH2:1]([N:3]([CH2:10][CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[C:12]([C:14]([C:20]#[N:21])=[C:15](C#N)[C:16]#[N:17])#[N:13].CCCCCC>CN(C=O)C.C(=O)([O-])O.[Na+]>[CH2:10]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:15]([C:16]#[N:17])=[C:14]([C:20]#[N:21])[C:12]#[N:13])=[CH:6][CH:5]=1)[CH3:11]

参加物

6

反応物 3

HCID 7061N,N-DiethylanilineHCID 8058HexaneHCID 12635Tetracyanoethylene

生成物 1

HCID 906081,1,2-Ethenetricarbonitrile, 2-(4-(diethylamino)phenyl)-収率 74%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

In an atmosphere of argon, 42.3 g (0.28 mol) of N,N-diethylaniline was dissolved in 570 ml of anhydrous DMF, and the solution obtained was cooled to 0° C., and then 46.3 g (1.25-fold equivalent weight) of tetracyanoethylene was added thereto. Then, the solution obtained was restored to room temperature, and stirred for 4.5 hours, which was thereafter poured in 1 liter of a saturated aqueous sodium hydrogencarbonate solution. The solid thus deposited was filtered to obtain a residue, and the residue was subjected to azeotropic distillation twice with 300 ml of toluene to remove the water content. Thereafter, 300 ml of ethyl acetate was added, and the atmosphere was replaced with argon, followed by heating at 80° C. for 1 hour to effect dissolution. To the mixture obtained, 800 ml of hexane was added with stirring, and the solution obtained was cooled to room temperature. The solid thus deposited was collected by filtration, and the residue obtained was vacuum-dried to obtain 51.7 g of N,N-diethyl-4-tricyanovinylaniline (yield: 74%).

後処理

  1. customthe solution obtained
  2. customThen, the solution obtained
  3. customwas restored to room temperature
  4. filtrationThe solid thus deposited was filtered
  5. customto obtain a residue
  6. distillationthe residue was subjected to azeotropic distillation twice with 300 ml of toluene
  7. customto remove the water content
  8. additionThereafter, 300 ml of ethyl acetate was added
  9. temperatureby heating at 80° C. for 1 hour
  10. dissolutiondissolution
  11. customTo the mixture obtained
  12. stirringwith stirring
  13. customthe solution obtained
  14. temperaturewas cooled to room temperature
  15. filtrationThe solid thus deposited was collected by filtration
  16. customthe residue obtained
  17. customwas vacuum-dried

出典と根拠

ORDレコード
ord-c823d718a0ea45b4aabb3a93f33f610c
出典データセット
uspto-grants-1998_11
特許番号
US05834575

関連ノート

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