Acetyl chloride → N-(2,2-Dimethoxyethyl)-N-2-propen-1-ylacetamide

HRID 1646104Notes

Reaction equation

HRID 1646104 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]([O:9][CH3:10])[O:7][CH3:8])[CH:2]=[CH2:3].[OH-].[Na+].[C:13](Cl)(=[O:15])[CH3:14]>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH2:5][CH:6]([O:9][CH3:10])[O:7][CH3:8])[C:13](=[O:15])[CH3:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 13334742N-(2,2-Dimethoxyethyl)prop-2-en-1-amine

Product 1

HCID 45120254N-(2,2-Dimethoxyethyl)-N-2-propen-1-ylacetamideYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

N-allyl-N-dimethoxyethyl amine (30% aqueous, 48.3 grams, 0.10 mole) was added to a glass reaction vessel fitted with a mechanical agitator. The agitator was started and sodium hydroxide (4.44 grams, 0.11 mole) was dissolved in the aqueous amine. Toluene (50 grams) was added and the mixture cooled to 0° to 5° C. Acetyl chloride (8.24 grams, 0.105 mole) was added over 10 minutes while maintaining the temperature below 5° C. The reaction mixture was stirred for 30 minutes at 5° C., agitation was stopped, and the mixture allowed to phase separate. The aqueous layer was discarded. Toluene was removed from the organic layer by rotary evaporation and 14.8 grams (0.08 mole) of N-allyl-N-dimethoxyethyl acetamide was isolated as confirmed by NMR.

Workup

  1. customfitted with a mechanical agitator
  2. temperaturethe mixture cooled to 0° to 5° C
  3. temperaturewhile maintaining the temperature below 5° C
  4. customseparate
  5. customToluene was removed from the organic layer by rotary evaporation

Sources & evidence

ORD record
ord-b3fdc222ce294d688cf8c9f09bac0102
Source dataset
uspto-grants-1993_01
Patent number
US05177263

Reaction notes

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