反応 #2501391

反応方程式

3-oxobutyric acid ethyl ester

1-phenylbiguanide

→

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

収率 74.0%

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-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-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 hexanes. 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′-phenylguanidine as a colorless solid (3.60 grams, 74 percent yield): mp=265° C.; 1H NMR (DMSO-d6, 303 K) δ: 11.19 (s, 1H), 9.05 (s, 1H), 9.5-6.5 (br, 2H), 7.65 (d, 2H, 3J=7.7 Hz), 7.26 (m, 2H), 7.00 (t, 1H, 3J=7.3 Hz), 5.60 (s, 1H), 2.09 (s, 3H); 13C NMR (DMSO-d6, 303 K) δ: 164.0, 163.2, 158.3, 156.2, 138.9, 128.8, 122.7, 120.7, 103.7, 23.6. Exact mass calculated for C12H13N5O=243.1120. Measured High Resolution Mass Spectrum (MAB/HR/N2)=243.1120. Anal. Calcd for C12H13N5O: C, 59.25; H, 5.39; N, 28.79. Found: C, 59.17; H, 5.39; N, 29.04.

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