Diethyl (ethoxymethylene)malonate → HCID 178469481, compound

HRID 439808Notes

Reaction equation

HRID 439808 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)=[CH:9][CH:8]=2)=[CH:5][NH:4][N:3]=1.C([O:25][CH:26]=[C:27]([C:33](OCC)=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])C.C[O-].[Na+]>C(O)C>[CH2:31]([O:30][C:28]([C:27]1[CH:33]=[N:1][C:2]2[N:3]([N:4]=[CH:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)=[CH:9][CH:8]=2)[C:26]=1[OH:25])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 10942334Sodium MethoxideHCID 178509247HCID 178509247, compound

Product 1

HCID 178469481HCID 178469481, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-amino-4-[4-(3,4-methylenedioxyphenylmethyl) phenyl]pyrazole (1.5 g) in ethanol (10 ml) was added diethyl ethoxymethylenemalonate (2.07 ml), and the mixture was heated and refluxed for 12 hours. To the mixture was added sodium methoxide (829 mg) under ice-cooling, and the mixture was stirred at room temperature for 1 day. The solvent 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 (2.1 g) at a quantitative yield.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 12 hours
  3. temperaturecooling
  4. distillationThe solvent 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-d805a14ef8b74d1bbfff45f594e919bc
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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