Sodium Chloride → N-(2,2-Dimethoxyethyl)-2-propenamide

HRID 1386524

Reaction equation

HRID 1386524 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][NH2:7].[C:10](Cl)(=[O:13])[CH:11]=[CH2:12].[Cl-].[Na+]>O.OC1CC(C)(C)[NH+]([O-])C(C)(C)C1>[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][NH:7][C:10](=[O:13])[CH:11]=[CH2:12]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide2×HCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 9898899N-(2,2-Dimethoxyethyl)-2-propenamideYield 81.7%

Reagents, catalysts & solvents 2

HCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxideCatalystHCID 962WaterSolvent

Procedure

40 g (1.0 mol) of sodium hydroxide are dissolved in 100 g of water and 200 g of ice in a 1 liter reactor fitted with stirring and cooling means. The sodium hydroxide solution is cooled to 10° C., and 105.1 g (1.0 mol) of aminoacetaldehyde dimethyl acetal and 10 mg of the inhibitor 4hydroxy-2,2,6,6-tetramethylpiperidine 1-oxide are added. 995 g (1.1 mol) of acryloyl chloride are slowly added to this solution at 10° C. over the course of 2 hours. The pH drops slowly and is finally set to pH=7. Amine is no longer present according to GC. The reaction mixture is saturated with sodium chloride and extracted three times with 200 ml of tert-butyl methyl ether. The organic phase is dried, filtered and evaporated on a rotary evaporator. The resultant oil is extracted three times with petroleum ether and subsequently re-dried on a rotary evaporator, giving 130 g of acrylamidoacetaldehyde dimethyl acetal (81% of theory) as an oil. The product is 99% pure according to GC.

Workup

  1. temperaturecooling means
  2. extractionextracted three times with 200 ml of tert-butyl methyl ether
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated on a rotary evaporator
  6. extractionThe resultant oil is extracted three times with petroleum ether
  7. customsubsequently re-dried on a rotary evaporator

Sources & evidence

ORD record
ord-8c56890eb1fd4b2b8e0f4d0de7ccb933
Source dataset
uspto-grants-2001_07
Patent number
US06265509B1

Linked notes

Loading…