Acetyl chloride → N-(4,4-diethoxybutyl)acetamide

HRID 376130Notes

Reaction equation

HRID 376130 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][CH2:6][CH2:7][NH2:8])[CH3:2].C(=O)([O-])O.[Na+].[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][CH2:7][NH:8][C:17](=[O:19])[CH3:18])[CH3:11]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 806724,4-DiethoxybutylamineHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

35.8 g (0.2 mol) of 4-aminobutyraldehyde-diethylacetal (90%) are dissolved in 600 ml of dichloromethane, 300 ml of saturated sodium hydrogen carbonate solution are added, and the mixture is cooled to 0° C. 17 ml (0.24 mol) of acetyl chloride are added dropwise at 0°-5° C., and the mixture is stirred for a further 6 hours at 0°-5° C. The organic phase is separated off and the aqueous phase is extracted twice more with dichloromethane. The organic phases are combined, dried over MgSO4, filtered and concentrated by evaporation in a rotary evaporator. The residue is purified by chromatography on silica gel with ethyl acetate. 4-(N-acetylamino)butyraldehyde-diethylacetal is obtained in the form of a yellowish oil.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted twice more with dichloromethane
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in a rotary evaporator
  6. customThe residue is purified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-f3b8b47df4804cdbbcecd06476fc3bee
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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