Ethyl Acetoacetate → HCID 178429545, compound

HRID 1785373Notes

Reaction equation

HRID 1785373 reaction equation
C(O[C:4](=[O:9])[CH2:5][C:6](=O)[CH3:7])C.[C:10]1([CH3:23])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]([NH:19][C:20]([NH2:22])=[NH:21])=[NH:18]>C(O)C>[CH3:7][C:6]1[N:21]=[C:20]([NH:19][C:17]([NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH3:23])=[NH:18])[NH:22][C:4](=[O:9])[CH:5]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178424376HCID 178424376, compound

Product 1

HCID 178429545HCID 178429545, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 milliliter round-bottom flask, 3-oxobutyric acid ethyl ester (2.6 grams, 0.020 mol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) was added at room temperature to a solution of 1-(o-tolyl)biguanide (3.8 grams, 0.020 mol; obtained from Aldrich Chemical Co.) in anhydrous ethanol (20 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 cold ethanol (0° C.). The solid was then recrystallized from anhydrous ethanol, recovered by filtration, and dried under reduced pressure to give the targeted N-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-N′-o-tolylguanidine as a colorless solid (3.50 grams, 68 percent yield): mp=260° C.; Exact mass calculated for C13H15N5O=257.1277. Measured Low Resolution Mass Spectrum (MAB/LR/N2)=257.1.

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 cold ethanol (0° C.)
  8. customThe solid was then recrystallized from anhydrous ethanol
  9. filtrationrecovered by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-a7566352028a4f13b59e1667f01710b1
Source dataset
uspto-grants-2009_03
Patent number
US07504502B2

Reaction notes

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