Acetic Anhydride → HCID 21872599, compound

HRID 895312Notes

Reaction equation

HRID 895312 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].OCC[N:11]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:13][OH:14].C(N(CC)CC)C.C1C[O:31][CH2:30][CH2:29]1>CN(C)C1C=CN=CC=1.O>[C:30]([O:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:31])[CH3:29]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11206303HCID 11206303, compound

Product 1

HCID 21872599HCID 21872599, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

At 20 to 30° C., acetic anhydride was added to a mixture of 9.29 g of N,N-bis(2-hydroxyethyl)-2-(methoxycarbonyl)ethylamine, 12.8 g of triethylamine, 50 mg of 4-dimethylaminopyridine and 50 ml of THF and the resulting mixture was stirred for 20 hours. Water was added to terminate the reaction. The reaction mixture was extracted with ethyl acetate. The organic layer was then washed with water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by distillation under reduced pressure, whereby 13.2 g of N,N-bis(2-acetoxyethyl)-2-(methoxycarbonyl)ethylamine was obtained (boiling point: 118 to 123° C./21 Pa, yield: 99%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was then 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-b59d167dff424546b752913c02d0af4c
Source dataset
uspto-grants-2005_07
Patent number
US06916593B2

Reaction notes

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