Zhang Da-yang
2004
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Journal
Fine chemicals
Abstract
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.