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

HRID 22614

반응식

HRID 22614 반응식
[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]

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide2회HCID 89728Aminoacetaldehyde dimethyl acetal

생성물 1

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

시약·촉매·용매 2

HCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxide촉매HCID 962Water용매

실험 절차

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 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 dimethyl-acetal and 10 mg of the inhibitor 4-hydroxy-2,2,6,6-tetramethylpiperidin-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 acrylamido-acetaldehyde dimethylacetal (81% of theory) are obtained in the form of an oil; the product is 99% according to GC.

후처리

  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

출처 및 근거

ORD 기록
ord-f913742319db48b68f8b62a82147532c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849210B2

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