Dimethylformamide → Diethyl benzyliminodiacetate

HRID 2308157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2308157
[NH:1]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])O.[Na+].CN(C)C=O.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([N:1]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 80502Diethyl iminodiacetateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 5235503Diethyl benzyliminodiacetateAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 5-L three-necked flask, 523.2 g (2.765 moles) of diethyl iminodiacetate, 465.4 g (5.540 moles) of sodium hydrogencarbonate and 1.4L of DMF (dimethylformamide) were put, and, keeping the mixture at about 40° C., 473.5 g (2.768 moles) of benzyl bromide was slowly dropwise added thereto with stirring. Thereafter, the mixture was stirred at about 40° C. for 16 hours. After the reaction was completed, 1.5L of water was added to the reaction product, which was then extracted with toluene (500 ml×four times). The organic layer formed was washed with water and dried with Glauber's salt. Thereafter, the solvent was evaporated to dryness to obtain 780 g of diethyl N-benzyliminodiacetate (yield: 98.8%).

Aufarbeitung

  1. customat about 40° C.
  2. stirringThereafter, the mixture was stirred at about 40° C. for 16 hours
  3. extractionwas then extracted with toluene (500 ml×four times)
  4. customThe organic layer formed
  5. washwas washed with water
  6. dry with materialdried with Glauber's salt
  7. customThereafter, the solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c15b1c20330f4a9cb11a4444279bc798
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06835471B2

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