Dimethylformamide → Diethyl benzyliminodiacetate

HRID 2308157Notes

Reaction equation

HRID 2308157 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 5235503Diethyl benzyliminodiacetateYield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c15b1c20330f4a9cb11a4444279bc798
Source dataset
uspto-grants-2004_12
Patent number
US06835471B2

Reaction notes

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