ChemicalBook CAS DataBase List Diethyl iminodiacetate

Diethyl iminodiacetate synthesis

5synthesis methods

Product Name:Diethyl iminodiacetate
CAS Number:6290-05-7
Molecular formula:C8H15NO4
Molecular Weight:189.21

64-17-5

142-73-4

6290-05-7

Ethanol was placed in a reaction flask at 0°C and stirred, thionyl chloride was added slowly and dropwise, and stirring was maintained until the temperature of the reaction mixture was raised to room temperature (about 30 min). Subsequently, iminodiacetic acid (3.33 g, 25 mmol) was added to the reaction system and the temperature of the reaction was raised to reflux and the reaction was continued overnight. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with saturated sodium bicarbonate solution (20 mL) and the pH was adjusted to neutral by adding solid sodium bicarbonate. After distillation under reduced pressure to remove most of the ethanol, the mixture was extracted three times with ethyl acetate (3 x 20 mL). The organic phases were combined, washed once with brine, dried through magnesium sulfate and filtered. Finally, the target product diethyl iminodiacetate (4.15 g, 88% yield) was obtained by distillation under reduced pressure (recovery of organic solvent).

142-73-4 Synthesis

142-73-4
442 suppliers
$6.00/25g

6290-05-7
233 suppliers
$27.00/50g

Yield:-

Reaction Conditions:

with thionyl chloride in ethanol;dichloromethane;water;N,N-dimethyl-formamide

Steps:

1.A Step A
Step A Synthesis of Iminodiacetic Acid Diethyl Ester A stirred solution of 931.0 grams (7.0 moles) of iminodiacetic acid and 1.0 ml of N,N-dimethylformamide in 5.25 liters of ethanol was cooled to 12° C. During a 1.5 hour period 2,100 grams (17.65 moles) of thionyl chloride was added dropwise to the cold solution. After complete addition the reaction mixture was heated at 60° C. for three hours, at reflux for two hours, then allowed to stand at room temperature for approximately 16 hours. The mixture was distilled at reduced pressure to remove 4.0 liters of ethanol leaving a liquid residue. The residue was dissolved in 4.0 liters of methylene chloride, then extracted with 3.5 liters of an aqueous 20% sodium carbonate solution. The aqueous extract was back washed with 1.0 liter of methylene chloride. The organic phases were combined, washed with 1.0 liter of water and evaporated under reduced pressure to leave a liquid. The liquid was purified by distillation under reduced pressure to yield 880.0 grams of iminodiacetic acid diethyl ester (b.p. 123° C./4.5 mmHg).

References:

FMC Corporation US4389528, 1983, A

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64-17-5 Synthesis

64-17-5
819 suppliers
$10.00/50g

142-73-4 Synthesis

142-73-4
442 suppliers
$6.00/25g

6290-05-7
233 suppliers
$27.00/50g

References

623-33-6 Synthesis