2-Methoxyethylamine → N-(2-methoxyethyl)acrylamide

HRID 975154노트

반응식

HRID 975154 반응식
C(N(CC)C(C)C)(C)C.[C:10](Cl)(=[O:13])[CH:11]=[CH2:12].[CH3:15][O:16][CH2:17][CH2:18][NH2:19]>ClCCl>[CH3:15][O:16][CH2:17][CH2:18][NH:19][C:10](=[O:13])[CH:11]=[CH2:12]

참가 물질

5

반응물 3

HCID 80182-MethoxyethylamineHCID 13140Acryloyl chlorideHCID 81531Diisopropylethylamine

생성물 1

HCID 11976962N-(2-methoxyethyl)acrylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N,N-Diisopropylethylamine (3.21 g, 25 mmol) was added to a stirred, ice-cooled solution of acryloyl chloride (2.25 g, 25 mmol) in dichloromethane (30 ml) under nitrogen followed, 2 minutes later, by 2-methoxyethylamine (1.92 g, 25.6 mmol) added dropwise over 1 hour. The cooling bath was removed, then the reaction mixture stirred for 18 hours at room temperature and washed twice with water. The combined aqueous washings were saturated with sodium chloride and exhaustively extracted with dichloromethane. All the dichloromethane solutions were combined, washed twice with 2M aqueous sodium carbonate solution, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of ethanol: dichloromethane (0:100 to 5:95), to yield the required amide as an oil. Rf 0.63 (SS 7). Found: C,54.97; H,9.24; N,10.68. C6H11NO2 ; 0.10 H2O requires C,55.04; H,8.62; N,10.70%. LRMS: m/z 130.4 (M+1)+.

후처리

  1. customThe cooling bath was removed
  2. washwashed twice with water
  3. extractionexhaustively extracted with dichloromethane
  4. washwashed twice with 2M aqueous sodium carbonate solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with a solvent gradient of ethanol: dichloromethane (0:100 to 5:95)

출처 및 근거

ORD 기록
ord-3c615f93ffa0409b87e1e3dc96dbe455
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05607960

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