تفاعل #2462461

معادلة التفاعل

water

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-ethyl-2-methylimidazole

phenylguanidine hydrogen carbonate

sodium methoxide

→

title compound

المردود 53.0%

2-Anilino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine

المردود 53.0%

المذيبات

DMA

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to ambient temperature
2. 2
   استخلاصThe solution was extracted EtOAc (2×50 ml)
3. 3
   غسيلThe combined extracts were washed with water (2×50 ml)
4. 4
   تجفيفbrine (2×50 ml), dried
5. 5
   أخرىthe volatiles removed by evaporation
6. 6
   أخرىThe residue was triturated with ether
7. 7
   ترشيحcollected by filtration and air
8. 8
   أخرىdried

الإجراء التجريبي

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-ethyl-2-methylimidazole (Method 23; 2.10 g, 10.1 mmol), phenylguanidine hydrogen carbonate (2.2 g, 11.1 mmol) and sodium methoxide (1.2 g, 22.2 mmol) were suspended in anhydrous DMA (15 ml) and the mixture heated at 110° C. for 18 hours. The reaction mixture was allowed to cool to ambient temperature and poured into water (50 ml). The solution was extracted EtOAc (2×50 ml). The combined extracts were washed with water (2×50 ml) and then brine (2×50 ml), dried and the volatiles removed by evaporation. The residue was triturated with ether, collected by filtration and air dried to give the title compound (1.48 g, 53%) as a reddish brown solid. NMR 1.17 (t, 3H), 2.38 (s, 3H), 4.52 (q, 2H), 6.93 (t, 1H), 7.08 (d, 1H), 7.27 (t, 2H), 7.60 (s, 1H),7.62 (d, 2H), 8.35 (d, 1H), 9.35 (s, 1H); m/z 280.

المصدر