Chemical Industry and Engineering Progree ›› 2012, Vol. 31 ›› Issue (04): 884-888.

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Synthesis of N-(5-amino-2,4-diethoxyphenyl)benzamide

  ZHAO DemingSONG JiabinWU ChunxinZHU SanqiJIN Ningren   

  1. College of Chemical Engineering and Materials Sciences,Zhejiang University of Technology,
    Hangzhou 310032,Zhejiang,China
  • Received:2011-09-13 Revised:2011-11-01 Online:2012-04-05 Published:2012-04-05

N-(5-氨基-2,4-二乙氧基苯基)苯甲酰胺的合成

赵德明,宋嘉彬,吴纯鑫,竺三奇,金宁人   

  1. 浙江工业大学化学工程与材料学院,浙江 杭州 310032
  • 通讯作者: 赵德明

Abstract: Through acylation and reduction reaction,N-(5-amino-2,4-diethoxyphenyl) benzamide(DEBAB)was synthesized from 2,4-diethoxy-5-nitroaniline(DEANB)and the experimental conditions,such as materials ratio,reaction temperature and reaction time,were investigated. Proper experimental conditions for acylation reaction were found as:n(DEANB)∶n(benzoyl chloride)= 1∶1.25,H2O and CH3OH as solvent,K2CO3 as deacid reagent reaction temperature 0 ℃,reaction time 1 h,the yield of N-(2,4-diethoxy-5-nitrophenyl) benzamide(DEBNB)was 90.95% based on DEANB and the purity was 98.35% as determined by HPLC;proper reduction reaction conditions were found as:n(DEBNB)∶n(Fe)= 1∶4,H2O and C2H5OH as solvent,reaction temperature 80 ℃,reaction time 5 h,pressure of hydrogen 1.5 MPa,the yield of DEDAB was 89.93% based on DEDNB and the purity was 98.96% as determined by HPLC. The molecular structures of product and its intermediates were identified by 1H-NMR,MS and FT-IR.

Key words: 2,4-diethoxy-5-nitroaniline(DEANB), N-(2,4-diethoxy-5-nitrophenyl) benzamide(DEBNB), N-(5-amino-2,4-diethoxyphenyl) benzamide(DEBAB), acylation reaction, reduction reaction, 2,4-diethoxy-5-nitroaniline(DEANB), N-(2,4-diethoxy-5-nitrophenyl) benzamide(DEBNB), N-(5-amino-2,4-diethoxyphenyl) benzamide(DEBAB), acylation reaction, reduction reaction

摘要: 2,4-二乙氧基-5-硝基苯胺(DEANB)为原料,先经酰化反应得到N-(2,4-二乙氧基-5-硝基苯基)苯甲酰胺(DEBNB),最后经还原得到蓝色基BB的同分异构体N-(5-氨基-2,4-二乙氧基苯基)苯甲酰胺(DEBAB)。DEBNB的较佳合成条件:n(DEANB):n(苯甲酰氯)=1∶1.25,丙酮和水作溶剂,K2CO3作缚酸剂,反应温度0 ℃,反应时间1 h,收率90.95%,HPLC纯度98.35%;产品DEBAB的较佳合成条件:Fe粉为还原剂,n(DEBNB):n(铁粉)=1∶4,水和乙醇作溶剂,反应时间5 h,反应温度80 ℃,收率89.93%,HPLC纯度98.96%。

关键词: 2, 4-二乙氧基-5-硝基苯胺, N-(2, 4-二乙氧基-5-硝基苯基)苯甲酰胺, N-(5-氨基-2, 4-二乙氧基苯基)苯甲酰胺, 酰化反应, 还原反应, 2,4-二乙氧基-5-硝基苯胺, N-(2,4-二乙氧基-5-硝基苯基)苯甲酰胺, N-(5-氨基-2,4-二乙氧基苯基)苯甲酰胺, 酰化反应, 还原反应

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