Water → diethyl {(E)-2-[3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]ethenyl}phosphonate

HRID 2221655Notes

Reaction equation

HRID 2221655 reaction equation
[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])P(=O)(OCC)OCC.[H-].[Na+].[CH3:20][NH:21][C:22]1[C:26]([CH:27]=O)=[CH:25][N:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:23]=1.O>CN(C)C=O>[CH3:20][NH:21][C:22]1[C:26](/[CH:27]=[CH:1]/[P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])=[CH:25][N:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 230763643-(methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86605743diethyl {(E)-2-[3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]ethenyl}phosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (5 mL) of tetraethyl methylenediphosphonate in N,N-dimethylformamide was added sodium hydride (60% in oil, 8.8 mg) at room temperature, and the mixture was stirred for 15 min. 3-(Methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde (1.00 g) was added to the reaction mixture, and the mixture was further stirred at room temperature for 2 hrs. Water was added to the reaction mixture and the mixture was stirred at room temperature for 2 hrs, and stood still for 16 hrs. The precipitated pale-yellow needle crystals were collected by filtration. The obtained crystals were recrystallized from ethyl acetate-hexane to give diethyl {(E)-2-[3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]ethenyl}phosphonate as pale-yellow needle crystals (1.45 g, yield 87%). melting point: 132-133° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hrs
  2. stirringthe mixture was stirred at room temperature for 2 hrs
  3. waitstood still for 16 hrs
  4. filtrationThe precipitated pale-yellow needle crystals were collected by filtration
  5. customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fe5ab231d9984317b59349e2c4a0997c
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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