Acetic Anhydride → N-(4,4-diethoxybutyl)acetamide

HRID 1613337Notes

Reaction equation

HRID 1613337 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:10][CH:11]([O:16][CH2:17][CH3:18])[CH2:12][CH2:13][CH2:14][NH2:15])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH2:17]([O:16][CH:11]([O:10][CH2:8][CH3:9])[CH2:12][CH2:13][CH2:14][NH:15][C:1](=[O:3])[CH3:2])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 806724,4-Diethoxybutylamine

Product 1

HCID 12677171N-(4,4-diethoxybutyl)acetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

20 g (196 mmol) of acetic anhydride in 100 ml of benzene are added drop by drop, at reflux, to a stirred suspension of 32 g (198 mmol) of 4,4-diethoxybutylamine and 24 g (174 mmol) of potassium carbonate in 600 ml of benzene. The mixture is heated to reflux for 15 min. and cooled, the precipitate is filtered and the filtrate is evaporated to dryness. The residual oil is treated with vegetable charcoal in 300 ml of diethyl ether and, after filtration and evaporation of the filtrate in vacuo, 37.3 g of oily product are obtained. n20D =1.4472.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 15 min.
  3. temperaturecooled
  4. filtrationthe precipitate is filtered
  5. customthe filtrate is evaporated to dryness
  6. additionThe residual oil is treated with vegetable charcoal in 300 ml of diethyl ether
  7. filtrationafter filtration and evaporation of the filtrate in vacuo, 37.3 g of oily product
  8. customare obtained

Sources & evidence

ORD record
ord-0e46ca5729fc476c9c192f5f10d5f890
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Reaction notes

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