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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (07): 810-814. 上一篇    下一篇

研究论文

1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-氨基吡唑及其酰胺、二酰亚胺的合成及晶体结构

杨芝萍1,2，钟平*,1，汤日元1，李术艳1   

  1. (1温州师范学院化学与材料科学学院 温州 325027)
  • 收稿日期:2004-11-26 修回日期:2005-01-13 发布日期:2005-06-30
  • 通讯作者: 钟平

Synthesis and Crystal Structure of 1-(2,6-Dichloro-4-trifluoromethyl- phenyl)-3-cyano-5-amino-pyrazole and Its Amides Plus Imide

YANG Zhi-Ping1,2,ZHONG Ping*,1,TANG Ri-Yuan1,LI Shu-Yan1   

  1. (1 School of Chemistry and Material Science, Wenzhou Normal College, Wenzhou 325027)
    (2 Department of Food and Biology Engineering, Zhangzhou Profession and Technical College, Zhangzhou 363000)
  • Received:2004-11-26 Revised:2005-01-13 Published:2005-06-30
  • Contact: ZHONG Ping

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2,6-二氯-4-三氟甲基苯胺经重氮化后与2,3-二氰基丙酸酯反应合成了1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-氨基吡唑(1), 1与乙酸酐、顺丁烯二酸酐、苯甲酰氯反应得到1的乙酰胺2a、顺丁烯酰亚胺2b和苯甲酰胺2c. 通过元素分析、红外光谱、核磁共振氢谱、核磁共振碳谱、质谱等手段对其结构进行了表征. 用X射线单晶衍射测定了化合物2a, 2b和2c的晶体结构. 2a属于单斜晶系, C2/c空间群, 晶胞参数a＝1.88282(6) nm, b＝0.86541(3) nm, c＝1.90766(6) nm, β＝95.5830(10)°, V＝3.09362 nm3, Z＝8, R＝0.064, wR＝0.170. 2b属于单斜晶系, P21/n空间群, 晶胞参数 a＝1.28261(10) nm, b＝0.89942(7) nm, c＝1.46896(12) nm, β＝104.217(1)°, V＝1.6427(2) nm3, Z＝4, R＝0.055, wR＝0.165. 2c属于三斜晶系, P-1空间群, 晶胞参数a＝0.84613(11) nm, b＝0.98923(13) nm, c＝1.14305(15) nm, β＝96.002(2)°, V＝0.9326 nm3, Z＝2, R＝0.0684, wR＝0.1795.

关键词: 2,6-二氯-4-三氟甲基苯胺, 晶体结构, 2,3-二氰基丙酸酯, 酰胺, 1-芳基-3-氰基-5-氨基吡唑

Reaction of 2,6-dichloro-4-trifluoromethylaniline with a suspension of nitrosyl sulphuric acid, followed by the reaction with a solution of ethyl 2,3-dicyanopropionate in acetic acid, gave 5-amino-3- cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (1), which was then reacted with acetic anhydride to give 2a, with maleic anhydride to yield 2b, and with benzoyl chloride to afford 2c. All compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and MS spectra. The crystal and molecular structures of 2a, 2b and 2c have been determined by single crystal X-ray diffraction analysis. Compound 2a belongs to monoclinic system with space group C2/c and a＝1.88282(6) nm, b＝0.86541(3) nm, c＝1.90766(6) nm, β＝95.5830(10)°, V＝3.09362 nm3, Z＝8, R＝0.0639, wR＝0.170. 2b belongs to monoclinic system with space group P21/n and a＝1.28261(10) nm, b＝0.89942(7) nm, c＝1.46896(12) nm, β＝104.217(1)°, V＝1.6427(2) nm3, Z＝4, R＝0.055, wR＝0.165. 2c belongs to triclinic sys-tem with space group P-1 and a＝0.84613(11) nm, b＝0.98923(13) nm, c＝1.14305(15) nm, β＝96.002(2)°, V＝0.9326 nm3, Z＝2, R＝0.0684, wR＝0.1795.

Key words: amide, 2,3-dicyanopropionate, crystal structur, 5-amino-3-cyano-1-arylpyrazole, 2,6-dichloro-4-trifluoromethylaniline