Cesium carbonate → 4-chloro-1-(4-methoxybutyl)-2-phenyl-1H-imidazole-5-carbaldehyde

HRID 1260037노트

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HRID 1260037 반응식
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].CS(O[CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[C:6]=1[CH:7]=[O:8]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 116870064-Methoxybutyl methanesulfonateHCID 178520008HCID 178520008, 화합물

생성물 1

HCID 583555004-chloro-1-(4-methoxybutyl)-2-phenyl-1H-imidazole-5-carbaldehyde수율 99.1%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
90 °C

실험 절차

To a solution of 4-chloro-2-phenyl-1H-imidazole-5-carbaldehyde (500 mg) and 4-methoxybutyl methanesulfonate (660 mg) in N,N-dimethylacetamide (10 ml) was added cesium carbonate (2.4 g); and the mixture was stirred at 90° C. for 7 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-3:7) was concentrated under reduced pressure to give the object product (702 mg).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (5:95-3:7)
  7. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-efae1479850a447aacbb1ef094b7e60d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466282B2

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