Acetic Anhydride → N-(2,2-Dimethoxyethyl)acetamide

HRID 1613328Notes

Reaction equation

HRID 1613328 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH2:18]>C1C=CC=CC=1>[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:18][C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 15289457N-(2,2-Dimethoxyethyl)acetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 32 g (313 mmol) of acetic anhydride in 200 ml of benzene is added, drop by drop, to a suspension, stirred and heated to reflux, of 40 g (290 mmol) of potassium carbonate and 30 g (285 mmol) of aminoacetaldehyde dimethyl acetal in 200 ml of benzene. Reflux is maintained for 30 min., then the mixture is cooled and filtered, the precipitate is washed with benzene, the filtrate is evaporated and the residual oil is treated with vegetable charcoal in 300 ml of diethyl ether. After filtration and evaporation, 36.8 g (250 mmol) of product are obtained. n25D =1.4450.

Workup

  1. temperatureheated
  2. temperatureReflux
  3. temperatureis maintained for 30 min.
  4. temperaturethe mixture is cooled
  5. filtrationfiltered
  6. washthe precipitate is washed with benzene
  7. customthe filtrate is evaporated
  8. additionthe residual oil is treated with vegetable charcoal in 300 ml of diethyl ether
  9. customare obtained

Sources & evidence

ORD record
ord-26350d100f024a0ab4561796ba80500d
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Reaction notes

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