N-[4-(4-溴丁氧基)-2-硝基苯基]乙酰胺的合成

以对乙酰氨基苯酚为原料,经烷基化、硝化合成N 4 (4 溴丁氧基) 2 硝基苯基]乙酰胺。用正交实验确定了烷基化反应的适宜条件为n(KOH)∶n(1,4 二溴丁烷)∶n(对乙酰氨基苯酚)=1 2∶2 8∶1,68～70℃反应80min,重结晶后收率为77 42%。硝化反应的适宜原料配比为n(HNO3)∶n(乙酸酐)∶n〔N 4 (4 溴丁氧基)苯基]乙酰胺〕=1 9∶9 6∶1,温度低于10℃反应收率可达92 2%。用薄层色谱、IR、1HNMR对产物进行了结构鉴定。分析目标产物及相关化合物的1HNMR谱,结果表明,在邻硝基乙酰苯胺及其衍生物中芳环上乙酰氨基邻位质子化学位移比按经验公式计算的预测值大0 6～1 3,这一特征是硝基和乙酰氨基相互作用的结果。

Synthesis of N-[4-(4-Bromobutoxy)-2-nitrophenyl]acetamide

N-4-(4-Bromobutoxy)-2-nitrophenyl]acetamide was synthesized from p-acetamidophenol via alkylation and nitration.The optimum alkylation reaction conditions were found by orthogonal test.At molar ratio of n(KOH)∶n(1,4-dibromobutane)∶n(p-acetamidophenol)=1.2∶2.8∶1 and 68～70 ℃ for 80 minutes,after recrystallization the yield of alkylation was 77.42%.Nitration with n(HNO_3)∶n〔(CH_3CO)_2O〕∶n〔N-4-(4-bromobutoxy)phenyl]-acetamide〕=1.9∶9.6∶1 was carried out at 10 ℃ to attain 92.2% yield.Structures of the products were confirmed by thin-layer chromatography,IR and ~1HNMR.In the molecules of o-nitroacetanilide and its derivatives,the chemical shift of neighbouring proton to acetamido group is 0.6～1.3 higher than the predicted value by empiric formula.It results from the interaction between nitro and acetamido groups.