1,1,3,3-Tetramethylguanidine → But-2-enedioic acid bis-[2-(2-dimethylamino-ethoxy)-ethyl]ester

HRID 1869114

反応式

HRID 1869114 の反応式
[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[C:10](Cl)(=[O:16])/[CH:11]=[CH:12]/[C:13](Cl)=[O:14].[CH3:18][N:19]([CH3:25])[C:20](N(C)C)=N>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:10](=[O:16])[CH:11]=[CH:12][C:13]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:20][N:19]([CH3:25])[CH3:18])=[O:14]

参加物

6

反応物 3

HCID 664601,1,3,3-TetramethylguanidineHCID 743482-(2-(Dimethylamino)ethoxy)ethanolHCID 5325504Fumaryl chloride

生成物 1

HCID 86609897But-2-enedioic acid bis-[2-(2-dimethylamino-ethoxy)-ethyl]ester収率 40.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒2 回

実験手順

The solution of 2-[2-(dimethylamino)-ethoxy]ethanol (6.65 g, 50 mmol, 2.5 equiv.) and 4-dimethylaminopyridine (11 mg) in toluene (20 ml) is cooled to −20° C. Separate solutions of fumaryl chloride (2.3 ml, 20 mmol, 1.0 equiv.) and 1,1,3,3-tetramethylguanidine (5.0 ml, 40 mmol, 2.0 equiv.) in toluene (each 25 ml) are added dropwise simultaneously via syringe pump over 80 min. A dark suspension is formed. After complete addition, the cooling bath is removed and stirring continued at 23° C. for 40 min. Active charcoal (1.0 g) is added and the mixture is filtered over a short pad of basic Al2O3, which is further rinsed with toluene/EtOAc (360 ml). The solution is concentrated and dried in vacuo (0.05 mbar) to yield the product as a yellow oil (2.79 g, 40%).

後処理

  1. customA dark suspension is formed
  2. additionAfter complete addition
  3. customthe cooling bath is removed
  4. additionActive charcoal (1.0 g) is added
  5. filtrationthe mixture is filtered over a short pad of basic Al2O3, which
  6. washis further rinsed with toluene/EtOAc (360 ml)
  7. concentrationThe solution is concentrated
  8. customdried in vacuo (0.05 mbar)

出典と根拠

ORDレコード
ord-1e196447fced4eac844e999ed22d99fe
出典データセット
uspto-grants-2009_12
特許番号
US07638118B2

関連ノート

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