Ethyl 3-oxohexanoate → HCID 178439477, compound

HRID 2222575Notes

Reaction equation

HRID 2222575 reaction equation
C(O[C:4](=[O:11])[CH2:5][C:6](=O)[CH2:7][CH2:8][CH3:9])C.[C:12]1([NH:18][C:19]([NH:21][C:22]([NH2:24])=[NH:23])=[NH:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[O:11]=[C:4]1[NH:24][C:22]([NH:21][C:19]([NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[NH:20])=[N:23][C:6]([CH2:7][CH2:8][CH3:9])=[CH:5]1

Participants

4

Reactant 2

HCID 238498Ethyl 3-oxohexanoateHCID 178513035HCID 178513035, compound

Product 1

HCID 178439477HCID 178439477, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 milliliter round-bottom flask, 3-oxohexanoic acid ethyl ester (3.2 grams, 0.020 mol, obtained from Aldrich Chemical Co., Milwaukee, Wis.) was added at room temperature to a solution of 1-phenylbiguanide (3.5 grams, 0.020 mol, prepared as described in Part D of Example I) in anhydrous ethanol (15 milliliters). The mixture was heated at reflux and stirred for 4 hours. After a few minutes, all the components dissolved. Cooling the resulting yellow solution mixture to room temperature gave a colorless precipitate. The precipitate was isolated by filtration and thoroughly washed with water, then with cold ethanol (0° C.), and finally with acetone. The solid was then recrystallized from anhydrous ethanol, recovered by filtration, and dried under reduced pressure to give the targeted N-(6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)-N′-phenylguanidine as a colorless solid (3.90 grams, 72 percent yield): mp=196° C.; Exact mass calculated for C14H17N5O=271.1433. Measured High Resolution Mass Spectrum (MAB/HR/N2)=271.1431. Anal. Calcd for C14H17N5O: C, 61.98; H, 6.32; N, 25.81. Found: C, 62.32; H, 6.44; N, 25.68.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. waitAfter a few minutes
  4. dissolutionall the components dissolved
  5. customgave a colorless precipitate
  6. customThe precipitate was isolated by filtration
  7. washthoroughly washed with water
  8. customwith cold ethanol (0° C.)
  9. customThe solid was then recrystallized from anhydrous ethanol
  10. filtrationrecovered by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-05f2186788124646a228f6982638a6cd
Source dataset
uspto-grants-2008_05
Patent number
US07371858B2

Reaction notes

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