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

HRID 481701Notes

Reaction equation

HRID 481701 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-litre reactor having a stirrer and a cooling system. The sodium hydroxide solution is cooled to 10° C., and 105.1 g (1.0 mol) of aminoacetaldehyde dimethylacetal and 10 mg of the inhibitor 4-hydroxy-2,2,6,6tetramethylpiperidin-1-oxide are added. 99.5 g (1.1 mol) of acrylic acid chloride are slowly added to that solution at 10° C. over a period of 2 hours. The pH value drops slowly and ultimately is adjusted to 7. According to GC, amine is no longer present. 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 concentrated using a rotary evaporator. The resulting oil is extracted three times with petroleum ether and then dried again using a rotary evaporator. 130 g of acrylamidoacetaldehyde dimethylacetal (81% of theory) are obtained in the form of an oil; the product is 99% according to GC.

Workup

  1. extractionextracted three times with 200 ml of tert-butyl methyl ether
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. extractionThe resulting oil is extracted three times with petroleum ether
  7. customdried again
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-6ade72ab78cc496ab77d33a64b507608
Source dataset
uspto-grants-1998_08
Patent number
US05789464

Reaction notes

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