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

HRID 1489649Notes

Reaction equation

HRID 1489649 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0753bc996e2b422c8fdf884135947011
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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