Reacción #2501388

Ecuación de reacción

3-oxoeicosanoic acid ethyl ester

1-phenylbiguanide

→

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

Rendimiento 58.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   TemperaturaThe mixture was heated
3. 3
   Temperaturaat reflux
4. 4
   Otrogave a colorless precipitate
5. 5
   OtroThe precipitate was isolated by filtration
6. 6
   Lavadothoroughly washed with water
7. 7
   Otrowith cold ethanol (0° C.)
8. 8
   OtroThe resulting powder was then recrystallized from anhydrous ethanol
9. 9
   Filtraciónrecovered by filtration
10. 10
    Otrodried under reduced pressure

Procedimiento

In a 50 milliliter round-bottom flask, 3-oxoeicosanoic acid ethyl ester (2.25 grams, 6.60 mmol, prepared as described in Part B of this Example) was added at room temperature to a solution of 1-phenylbiguanide (1.17 grams, 6.60 mmol, prepared as described in Part D of this Example) in anhydrous ethanol (20 milliliters). The mixture was heated at reflux and stirred for 16 hours. Cooling the resulting yellow solution 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 pentane. The resulting powder was then recrystallized from anhydrous ethanol, recovered by filtration, and dried under reduced pressure to give the targeted N-(4-heptadecyl-6-oxo-1,6-dihydropyrimidin-2-yl)-N′-phenylguanidine as a colorless solid (1.79 grams, 58 percent yield): mp=164° C.; 1H NMR (DMSO-d6, 303 K) δ: 11.16 (s, 1H), 9.04 (s, 1H), 8.5-6.5 (br, 2H), 7.66 (d, 2H, 3J=7.9 Hz), 7.25 (m, 2H), 6.99 (t, 1H, 3J=7.4 Hz), 5.56 (s, 1H), 2.32 (t, 1H, 3J=7.5 Hz), 1.56 (m, 2H), 1.33-1.17 (m, 28H), 0.85 (t, 3H, 3J=6.8 Hz); Exact mass calculated for C28H45N5O=467.3624. Measured Low Resolution Mass Spectrum MAB/LR/N2)=468.2. Anal. Calcd for C28H45N5O: C, 71.91; H, 9.70; N, 14.97. Found: C, 72.02; H, 9.96; N, 14.92.

Fuente