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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (01): 82-86. 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-氨基吡唑及其磺酰胺的合成及晶体结构

杨芝萍1,2，钟平*,1，李术艳1，汤日元1   

  1. (1温州师范学院化学与材料科学学院 温州 325027)
    (2漳州职业技术学院食品与生物工程系 漳州 363000)
  • 收稿日期:2005-03-08 修回日期:2005-08-01 发布日期:2005-12-31
  • 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 Sulfonic Amides

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

  1. (1 School of Chemistry and Material Science, Wenzhou Normal College, Wenzhou 325027)
    (2 Department of Food and Biology Engineering, Zhangzhou Profession and Tech-nical College, Zhangzhou 363000)
  • Received:2005-03-08 Revised:2005-08-01 Published:2005-12-31
  • 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与苯磺酰氯、对甲基苯磺酰氯、甲基磺酰氯反应, 得到1的苯磺酰胺2a、对甲基苯磺酰胺2b和双甲基磺酰胺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1, 2a和2c的晶体结构. 1属于正交斜方晶系, Pbca空间群, 晶胞参数 a＝1.61739(7) nm, b＝1.62480(7) nm, c＝3.10857(13) nm, ＝＝＝90, V＝8.1691 nm3, Z＝24, R＝0.1089, wR＝0.2545. 2a属于单斜晶系, C2/c空间群, 晶胞参数 a＝3.35144(18) nm, b＝0.97948(5) nm, c＝2.44717(12) nm, β＝102.460(1), V＝7.8440(7) nm3, Z＝8, R＝0.1831, wR＝0.2600. 2c属于三斜晶系, P-1空间群, 晶胞参数 a＝0.84681(7) nm, b＝0.89652(83) nm, c＝1.43497(12) nm, α＝75.198(2), β＝87.918(1), γ＝65.395(1), V＝0.9546 nm3, Z＝2, R＝0.049, wR＝0.135.

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, 1-芳基-3-氰基-5-氨基吡唑, 磺酰胺

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 benzenesulfonyl chloride to yield 2a, with 4-methylbenzenesulfonyl chloride to 2b, and with methansulfonyl chloride to 2c. All compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and MS spectra. The crystal and molecular structures of 1, 2a and 2c have been determined by single crystal X-ray diffraction analysis. Compound 1 belongs to orthorhombic system with space group Pbca and a＝1.61739(7) nm, b＝1.62480(7), c＝3.10857(13) nm, α＝β＝γ＝90, V＝8.1691 nm3, Z＝24, R＝0.1089, wR＝0.2545, 2a to monoclinic system with space group C2/c and a＝3.35144(18) nm, b＝0.97948(5) nm, c＝2.44717(12) nm, β＝102.460(1), V＝7.8440(7) nm3, Z＝8, R＝0.1831, wR＝0.2600, and 2c to triclinic sys-tem with space group P-1 and a＝0.84681(7) nm, b＝0.89652(83) nm, c＝1.43497(12) nm, α＝75.198(2), β＝87.918(1), γ＝65.395(1), V＝0.9546 nm3, Z＝2, R＝0.049, wR＝0.135.

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