反応 #2501389

反応方程式

3-oxohexanoic acid ethyl ester

1-phenylbiguanide

→

N-(6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)-N′-phenylguanidine

収率 72.0%

溶媒

ethanol

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux
3. 3
   workup.WAITAfter a few minutes
4. 4
   workup.DISSOLUTIONall the components dissolved
5. 5
   その他gave a colorless precipitate
6. 6
   その他The precipitate was isolated by filtration
7. 7
   洗浄thoroughly washed with water
8. 8
   その他with cold ethanol (0° C.)
9. 9
   その他The solid was then recrystallized from anhydrous ethanol
10. 10
    ろ過recovered by filtration
11. 11
    その他dried under reduced pressure

実験手順

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.

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