Chloroacetaldehyde → 2-(3-methoxyphenyl)-1-phenyl-1H-imidazole

HRID 539483

반응식

HRID 539483 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6](=[NH:14])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:19][CH:20]=O.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:19]=[CH:20][N:14]=2)[CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 178490388HCID 178490388, 화합물

생성물 1

HCID 571284632-(3-methoxyphenyl)-1-phenyl-1H-imidazole수율 75.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a 500 mL round bottom flask was added 3-methoxy-N-phenylbenzimidamide (7.81 g, 34.5 mmol), 2-chloroacetaldehyde solution (50%, 9.4 mL, 69 mmol), sodium bicarbonate (5.80 g, 69 mmol), and 150 mL 2-propanol. The reaction mixture was heated at reflux for 3 h under nitrogen. The solvent was removed under vacuum and the residue dissolved in ethyl acetate. The ethyl acetate solution was washed with water, brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography eluting with 50% and 100% ethyl acetate/hexane to give pure product (6.52 g, 75%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h under nitrogen
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography
  10. washeluting with 50% and 100% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-9dbcc9fbbfd64b0e8b40a96957ed0d9f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871361B2

연결된 노트

불러오는 중…