Ethanol → HCID 13769871, compound

HRID 570015Notes

Reaction equation

HRID 570015 reaction equation
[Na].S(O)(O)(=O)=O.[C:7]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)(=[NH:9])[NH2:8].C(O[CH:26]=[C:27]([C:33]([C:35]([OH:37])=[O:36])=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])C.[CH2:38](O)[CH3:39]>>[CH2:16]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[N:8]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][N:9]=2)[CH2:11][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 5360545SodiumHCID 54255144Ethoxymethylene oxalacetic acid ethyl ester

Product 1

HCID 13769871HCID 13769871, compoundYield 96%

Procedure

To absolute ethanol with 0.91 g of sodium dissolved therein, 11.5 g of 1-amidino-4-benzylpiperazine sulfate was added. The resultant mixture was stirred at room temperature for 30 minutes, to which 8.8 g of ethyl ethoxymethyleneoxaloacetate [synthesized by the process described in J. Am. Chem. Soc., 73, 3684 (1951)] was added. After allowing them to react at room temperature for 2 days, the reaction was caused to proceed further for 1 hour while heating the reaction mixture under reflux. After cooling the reaction mixture to room temperature, ethanol was distilled off under reduced pressure and the residue was dissolved in a mixture of water and ethyl acetate. After separation of the water layer, the ethyl acetate layer was washed with water and then with saturated saline. After drying the ethyl acetate layer with magnesium sulfate, ethyl acetate was distilled off under reduced pressure to obtain 13.7 g of the above-identified compound as light brown crystals (yield: 96%).

Workup

  1. customsynthesized by the process
  2. addition, 73, 3684 (1951)] was added
  3. customto react at room temperature for 2 days
  4. temperaturewhile heating the reaction mixture
  5. temperatureunder reflux
  6. distillationethanol was distilled off under reduced pressure
  7. dissolutionthe residue was dissolved in a mixture of water and ethyl acetate
  8. customAfter separation of the water layer
  9. washthe ethyl acetate layer was washed with water
  10. dry with materialAfter drying the ethyl acetate layer with magnesium sulfate, ethyl acetate
  11. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-a01e75ffd96d4cdf86e410cb6dbd5ed1
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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