N-[4-(磺酰胺)苯基](甲基)丙烯酰胺的合成

Synthesis of N-[4-(aminosulfonyl)phenyl](meth)acrylamide

以对氨基苯磺酰胺、丙烯酰氯(或甲基丙烯酰氯)为原料合成了N[4(磺酰胺)苯基]丙烯酰胺(ASPAA)和N[4(磺酰胺)苯基]甲基丙烯酰胺(ASPMAA),其结构经1HNMR,IR和元素分析表征。合成ASPAA的最佳条件对氨基苯磺酰胺13.76g(80mmol),n(对氨基苯磺酰胺)∶n(丙烯酰氯)=1.0∶1.1,n(丙烯酰氯)∶n(NaHCO3)=1.00∶1.14,0℃～2℃反应3h,反应液倾入10倍体积的的甲醇-水[V(甲醇)∶V(水)=1∶10]中析出产物,收率在60%以上。合成ASPMAA的最佳条件对氨基苯磺酰胺6.88g(40mmol),n(对氨基苯磺酰胺)∶n(甲基丙烯酰氯)=1.00∶1.05,n(三己胺)∶n(甲基丙烯酰氯)=1.0∶1.0,在0℃～2℃滴加甲基丙烯酰氯后先在室温下反应1h,然后在60℃反应1h,反应液倾入700mL石油醚中析出产物,收率50%～60%。

N-[4-(aminosulfonyl)phenyl]acrylamide(ASPAA) and N-[4-(aminosulfonyl)phenyl]methacrylamide (ASPMAA) were synthesized through the reaction of acryloyl chloride or methacryloyl chloride with sulfonamide(SA). Their structures were confirmed by 1H NMR, IR and elemental analysis. It was showed that relative higher yields were achieved when the reaction conditions were optimized as follows: for ASPAA, SA was 13.76 g(80 mmol), the molar ratio of SA and sodium hydrogen carbonate with acryloyl chloride at 1.00 ∶1.10 and 1.14 ∶1.00, the reaction mixture precipitated in methanol/water(V ∶V ~1 ∶10), after reaction at 0 ℃~2 ℃ for 3h; for ASPMAA, SA was 6.88 g(40 mmol), the molar ratio of SA and triethylamine with methacryloyl chloride at 1.0 ∶1.05 and ~1.0 ∶1.0, the reaction mixture precipitated in 700 mL petroleum ether, after dropping methacryloyl chloride at 0 ℃~2 ℃ and reacting at room temperature for 1 h then at 60 ℃ for 1 h.