Hydrochloric Acid → (E)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)acrylamide

HRID 2264785노트

반응식

HRID 2264785 반응식
CN(C)CC(O)=O.C([O-])(=O)C.[Na+].Br[C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:17]([O:19][CH3:20])=[O:18].[CH:26]([N:29]([CH:34]([CH3:36])[CH3:35])[C:30](=[O:33])[CH:31]=[CH2:32])([CH3:28])[CH3:27].Cl>ClCCl.CN1CCCC1=O>[CH:34]([N:29]([CH:26]([CH3:28])[CH3:27])[C:30](=[O:33])/[CH:31]=[CH:32]/[C:14]1[CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:36])[CH3:35]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 517045Sodium AcetateHCID 559397N,N-Diisopropylacrylamide2회HCID 611662Methyl 3-bromo-4-methoxybenzoate2회

생성물 1

HCID 22735209(E)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)acrylamide수율 69%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
130 °C

실험 절차

A stirred suspension consisting of N,N-dimethylglycine (6.0 mmol), anhydrous sodium acetate (40 mmol), methyl 3-bromo-4-methoxybenzoate (20 mmol, 4.90 g), N,N-diisopropylacrylamide (24 mmol, 3.72 g), bis-(benzonitrile)-palladium-II chloride (1.5 mol %), and 20 ml of N-methyl-2-pyrrolidinone was heated at 130° C. until no starting material could be detected by tlc (starting material methyl 3-bromo-4-methoxybenzoate: RE 0.73; N,N-diisopropylacrylamide: Rf 0.46; solvent system (1)). After cooling to room temperature 50 ml of an aqueous 2N HCl solution was added. The reaction was diluted with dichloromethane (50 ml) and the precipitated grey palladium metal was filtered off. The organic phase was washed with five portions (50 ml each) of 2N aqueous hydrochloric acid, dried (MgSO4) and evaporated to dryness. The remaining off-white solid was recrystallized from ethyl acetate/n-hexane to give 4.40 g (E)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-acrylamide in 69% yield, m.p. 139-140° C., tlc: (1) Rf 0.40. NMR (CD2Cl2): 21.22, 22.10, 46.39, 48.87, 52.59, 56.61, 111.42, 123.39, 123.78, 125.54, 130.32, 132.53, 135.07.

후처리

  1. additionwas added
  2. filtrationthe precipitated grey palladium metal was filtered off
  3. washThe organic phase was washed with five portions (50 ml each) of 2N aqueous hydrochloric acid
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe remaining off-white solid was recrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-5bfb323a6bde44319ba02de25dac9eb0
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855230B2

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