Title

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體結構

Translated Titles

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

Authors

楊芝萍(Zhi-Ping Yang);鍾平(Ping Zhong);李術豔(Shu-Yan Li);湯日元(Ri-Yuan Tang)

Key Words

2,6-二氯-4-三氟甲基苯胺 ; 2,3-二氰基丙酸酯 ; 1-芳基-3-氰基-5-氨基吡唑 ; 磺酰胺 ; 晶體結構 ; 2,6-dichloro-4-trifluoromethylaniline ; 2,3-dicyanopropionate ; 5-amino-3-cyano-1-arylpyrazole ; sulfonic amide ; crystal structure

PublicationName

有機化學

Volume or Term/Year and Month of Publication

26卷1期(2006 / 01 / 01)

Page #

82 - 86

Content Language

簡體中文

Chinese Abstract

2,6-二氯-4-三氟甲基苯胺經重氮化後與2,3-二氰基丙酸酯反應合成了1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-氨基吡唑(1),1與苯磺酰氯、對甲基苯磺酰氯、甲基磺酰氯反應,得到1的苯磺酰胺2a、對甲基苯磺酰胺2b和雙甲基磺酰胺2c。通過元素分析、紅外光譜、核磁共振氫譜、核磁共振碳譜、質譜等手段對其結構進行了表徵。用X射線單晶衍射測定了化合物1,2a和2c的晶體結構。1屬於正交斜方晶系,Pbca空間群,晶胞參數a=1.61739(7) nm,b=1.62480(7) nm,c=3.10857(13) nm,a=β=γ=90°,V=8.1691 nm^3,Z=24,R=0.1089,wR=0.2545,2a屬於單斜晶系,C2/c空間群,晶胞參數a=3.35144(18) nm,b=0.97948(5) nm,c=2.44717(12) nm,β=102.460(l)°,V=7.84407(7) nm^3,Z=8,R=0.1831,wR=0.2600。2c屬於三斜晶系,P-l空間群,晶胞參數a=0.84681(7) nm,b=0.89652(83) nm,c=1.43497(12) nm,α=75.198(2)°,β=87.918(l)°,γ=65.395(l)°,V=0.9546nm^3,Z=2,R=0.049,wR=0.135。

English Abstract

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) nm, c=3.10857(13) nm, a=β=γ=90°, V=8.1691 nm^3, Z=24, R=0.1089, wR0.2545, 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) nm^3, Z=8, R=0.1831, wR=0.2600, and 2c to triclinic system with space group P-l and a=0.84681(7) nm, b=0.89652(83) nm, c=1.43497(12) nm, a=75.198(2)°, β=87.918(1)°, γ=65.395(l)°, V=0.9546 nm^3, Z=2, R=0.049, wR=0.135.

Topic Category 基礎與應用科學 > 化學