Diethyl (ethoxymethylene)malonate → HCID 178469481, compound

HRID 1654734Notes

Reaction equation

HRID 1654734 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 filtration, 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 filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-5317499fdc0b493c99b76f8afc8bacd4
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

Loading…