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

HRID 22614

反応式

HRID 22614 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 9898899N-(2,2-Dimethoxyethyl)-2-propenamide収率 81.7%

試薬・触媒・溶媒 2

HCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxide触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f913742319db48b68f8b62a82147532c
出典データセット
uspto-grants-2005_02
特許番号
US06849210B2

関連ノート

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