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

HRID 1078349ノート

反応式

HRID 1078349 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-55557e33f83d47dcbe8eef3e8f368841
出典データセット
uspto-grants-1996_08
特許番号
US05547967

反応ノート

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