Diethyl (ethoxymethylene)malonate → HCID 178469483, compound

HRID 439805Notes

Reaction equation

HRID 439805 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([CH3:15])[CH3:14])=[CH:9][CH:8]=2)=[CH:5][NH:4][N:3]=1.C([O:24][CH:25]=[C:26]([C:32](OCC)=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28])C.C[O-].[Na+]>C(O)C>[CH2:30]([O:29][C:27]([C:26]1[CH:32]=[N:1][C:2]2[N:3]([N:4]=[CH:5][C:6]=2[C:7]2[CH:8]=[CH:9][C:10]([C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([CH3:15])[CH3:14])=[CH:11][CH:12]=2)[C:25]=1[OH:24])=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 10942334Sodium MethoxideHCID 178438916HCID 178438916, compound

Product 1

HCID 178469483HCID 178469483, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspention of 3-amino-4-[4-(2-phenylpropan-2-yl) phenyl]pyrazole (920 mg) in ethanol (10 ml) was added diethyl ethoxymethylenemalonate (1.34 ml), and the mixture was heated and refluxed for 3 days. To the mixture was added sodium methoxide (540 mg) under ice-cooling, and the mixture was stirred for 1 day. Ethanol was distilled away under reduced pressure, and thereto was added water (50 ml) under ice-cooling. The mixture was adjusted to acid with 10% hydrochloric acid, and the precipitate was separated by filtraltion, washed with water to give the title compound (1.26 g, 94.6%).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 3 days
  3. temperaturecooling
  4. distillationEthanol was distilled away under reduced pressure
  5. additionwas added water (50 ml) under ice-
  6. temperaturecooling
  7. customthe precipitate was separated by filtraltion
  8. washwashed with water

Sources & evidence

ORD record
ord-6acb7f3d16634036803d747c5a04450e
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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