Diethyl (ethoxymethylene)malonate → HCID 178469815, compound

HRID 570006Notes

Reaction equation

HRID 570006 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[C:8]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(=[NH:10])[NH2:9].C([O:26][CH:27]=[C:28]([C:34](OCC)=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30])C>C(O)C>[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[N:9]=[C:27]([OH:26])[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:34][N:10]=2)[CH2:12][CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfate

Product 1

HCID 178469815HCID 178469815, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution of 25.2 g of sodium hydroxide was added with 160 g (0.60 mol) of 1-amidino-4-benzylpiperazine sulfate, followed by a dropwise addition of 129.4 g (0.60 mol) of diethyl ethoxymethylenemalonate over 20 minutes. After being refluxed for 5.5 hours, the reaction mixture was cooled and the precipitated crystals were collected by filtration. The thus-obtained crystals were washed with water and then dried, thereby obtaining 131.4 g of the above-identified compound (yield: 64%).

Workup

  1. temperatureAfter being refluxed for 5.5 hours
  2. temperaturethe reaction mixture was cooled
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThe thus-obtained crystals were washed with water
  5. customdried

Sources & evidence

ORD record
ord-4f8d268c255d4bcc9493bf3ff2360d98
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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