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7-氨基-6-硝基苯并二氧化呋咱的合成研究 被引量:7

Synthesis of 7-Amino-6-nitrobenzodifuroxan
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摘要 以3,5-二氯苯胺为原料经过4步反应合成了7-氨基-6-硝基苯并二氧化呋咱(ANBDF)。在四氢呋喃溶剂中-3,5-二氯苯胺与氯乙酰氯反应得到3,5-二氯-N-氯乙酰基苯胺(Ⅰ),收率97.7%;(Ⅰ)在室温下于浓硫酸(98%)-发烟硝酸(98%)中硝化2h,得到3,5-二氯-2,4,6-三硝基-N-氯乙酰苯胺(Ⅱ),收率92.3%。(Ⅱ)在冰乙酸中,与NaN,反应,不经分离直接在110℃下进行热解脱氮得到7-氯乙酰氨基-6-硝基苯并二氧化呋咱(Ⅲ),收率82.5%。(Ⅲ)碱性水解得到目标化合物7-氨基-6-硝基苯并二氧化呋咱(Ⅳ),熔点204~205℃,收率66%。讨论了关键反应的影响因素,并通过红外光谱、核磁共振、质谱及元素分析确定了目标化合物及其中间体的结构。 7-Amino-6-nitrobenzodifuroxan (ANBDF) was prepared through a four-step reaction process using 3, 5-dichloroaniline as starting material.3,5-dichloro-N-chloroacetaniline ( Ⅰ) was prepared in 97.7% yield by the reaction of chloro-acetic chloride with 3,5-dichloroaniline in the media of THF. Nitration of the compound ( Ⅰ ) with a mixture of fuming nitric acid (98%) and concentrated sulphuric acid (98%) at room temperature for 2 h gave 3,5-dichloro-2,4,6- trinitro-N-chloroacetaniline (Ⅱ) in 92.3% yield. 7-Chloroacetamide-6-nitrobenzodifuroxan (Ⅲ) was obtanined in 82.5% yield from ( Ⅱ ) and sodium azide in acetic acid through denitrogenization at 110 ℃. The title compound (Ⅳ) was prepared by hydrolyzing of (Ⅲ) in basic media with a yield of 66% .The melting point of Ⅳ is 204 ~ 205℃.The factors affecting the key reactions were discussed. The structures of 7-amino-6-nitrobenzodifuroxan and its three intermediates have all been determined by IR,^1H NMR, MS and elemental analysis.
出处 《化学世界》 CAS CSCD 北大核心 2006年第8期484-486,462,466,共5页 Chemical World
关键词 7-氨基-6-硝基苯并二氧化呋咱 苯并氧化呋咱 合成 表征 7-amino-6-nitrobenzodifuroxan benzofuroxan synthesis characterization
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参考文献4

  • 1Ammon H L,Bhattacharijee S B.Crystallographic studies of high-desity organic compounds:4-amino-5-nitrobenzo[1,2-c:3,4-c'] bis[1,2,5] oxadiazole-3,8-dioxide[J].Acta Cryst.1982,B38:2498-2503.
  • 2Koppes W M,Lawrence G W,Sitzmann M E,et al.Reaction of 1,3,5-trifluoro trinitrobenzene with nucleophiles[J].J C S.Perkin I,1981,1815-1820.
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  • 4王建龙.苯并氧化呋咱含能衍生物的合成、结构及性能研究[D].北京:北京理工大学,2003.

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