Acetic Anhydride → HCID 21872395, compound

HRID 895314Notes

Reaction equation

HRID 895314 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC[N:11]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].C(N(CC)CC)C.C1COCC1>CN(C)C1C=CN=CC=1.O>[C:5]([O:4][CH2:1][CH2:2][N:11]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12193781HCID 12193781, compound

Product 1

HCID 21872395HCID 21872395, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

At 20 to 30° C., 2.56 g of acetic anhydride was added to a mixture of 5.00 g of N-(2-hydroxyethyl)bis[2-(methoxycarbonyl)ethyl]amine, 2.97 g of triethylamine, 50 mg of 4-dimethylaminopyridine and 25 g of THF. The resulting mixture was stirred for 5 hours. Water was added to terminate the reaction. The reaction mixture was then extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by distillation under reduced pressure, whereby 5.30 g of N-(2-acetoxyethyl)bis[2-(methoxycarbonyl)ethyl]amine was obtained (boiling point: 120° C./15 Pa, yield: 92%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe reaction mixture was then extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. distillationthe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-9f7b83b45e32450b84350119009beff6
Source dataset
uspto-grants-2005_07
Patent number
US06916593B2

Reaction notes

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