Potassium Carbonate → 3-{5-[N-(2-(3,4-dimethyloxyphenyl)-ethyl)-N-methylaminocarbonyl]-pentyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole

HRID 1078349노트

반응식

HRID 1078349 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][N:35]([CH3:44])[C:36]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]Br)=[O:37])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]>CN(C)C=O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][N:35]([CH3:44])[C:36]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][O:16][C:13]2[CH:12]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:15][N:14]=2)=[O:37])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 220460885-(3,4-Dimethoxyphenyl)-pyrazolin-3-oneHCID 229023315-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminocarbonyl}-pentyl bromide

생성물 1

HCID 229023223-{5-[N-(2-(3,4-dimethyloxyphenyl)-ethyl)-N-methylaminocarbonyl]-pentyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole수율 84.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
100 °C

실험 절차

3.85 g of 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one were dissolved in 50 ml of anhydrous dimethylformamide. 3.15 g of finely ground potassium carbonate were added to the solution, and the reaction mixture was heated under a nitrogen atmosphere to 100° C. with stirring. A solution of 5.6 g of 5-{N-[2-(3,4-dimethoxyphenyl)-ethyl]-N-methylaminocarbonyl}-pentyl bromide in 10 ml of anhydrous dimethyl formamide was slowly added dropwise to the solution, and the reaction mixture was stirred at 100° C. for a further 2 hours. In order to work up the reaction mixture, it was cooled and then the precipitated salts were filtered out and the filtrate was concentrated by evaporation. The oily residue which remained was dissolved in ethyl acetate and washed with 7% strength sodium hydroxide solution in order to remove unreacted 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one. The organic phase was separated, dried with sodium sulfate and concentrated by evaporation. 6.5 g of 3-{5-[N-(2-(3,4-dimethyloxyphenyl)-ethyl)-N-methylaminocarbonyl]-pentyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole were obtained as an oil.

후처리

  1. stirringthe reaction mixture was stirred at 100° C. for a further 2 hours
  2. temperaturewas cooled
  3. filtrationthe precipitated salts were filtered out
  4. concentrationthe filtrate was concentrated by evaporation
  5. dissolutionThe oily residue which remained was dissolved in ethyl acetate
  6. washwashed with 7% strength sodium hydroxide solution in order
  7. customto remove unreacted 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one
  8. customThe organic phase was separated
  9. dry with materialdried with sodium sulfate
  10. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-55557e33f83d47dcbe8eef3e8f368841
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05547967

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