文章摘要
朱为宏.5-氨基-1-苄基-4-氰基吡唑的合成及晶体结构研究[J].精细化工,2015,32(6):0
5-氨基-1-苄基-4-氰基吡唑的合成及晶体结构研究
5-Amino-1-benzyl-4-cyano-pyrazole: Synthesis and Crystal Structure
投稿时间:2014-11-25  修订日期:2015-01-22
DOI:
中文关键词: 5-氨基-1-苄基-4-氰基吡唑  合成  晶体结构
英文关键词: 5-amino-1-benzyl-4-carbonitrile-pyrazole  synthesis  crystal structure
基金项目:国家自然科学基金(21176075)
作者单位E-mail
朱为宏 华东理工大学 精细化工研究所 whzhu@ecust.edu.cn 
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中文摘要:
      由于低的区域选择性,3-氨基-4-氰基吡唑进行烷基化反应均不能产生单一产物。该文采用烷基化合成路线,以3-氨基-4-氰基吡唑为原料,考察了反应溶剂和碱性的缚酸剂对苄基化产物的选择性、产率影响,在以DMSO、DMF和CH3CN作为溶剂时,反应总转化率相差并不明显,但从区域选择性来看, DMSO中反应选择性最好,可采用简单的95%乙醇重结晶即可得到5-氨基-1-苄基-4-氰基吡唑。通过工艺优化,以DMSO为溶剂,碳酸铯为反应缚酸剂,在100 ℃下反应,得到了纯度超过98%合格的产品,重结晶收率后收率达到62%,产物通过1HNMR和X射线衍射进行了结构表征。单晶X衍射表明,5-氨基-1-苄基-4-氰基吡唑的晶体为单斜晶系,P2(1)c空间群,a = 1.4333(3) nm, b = 0.6187(14) nm,c = 2.2389 (5) nm,α = 90°,β = 93.773(4)°,γ = 90°,V = 1.981.1(8) nm3, Z = 8,Dc = 1.329 g cm-3,λ = 0.71073 nm,μ (Mo Kα) = 0.085 mm-1,F(000) = 832。
英文摘要:
      Due to the low region-selectivity, the alkylation of 5-amino-4-cyano-pyrazole always bring forth the mixture of two substitution products. Based on the alkylation method, We start from the raw material of 3-amino-1H-pyrazole-4-carbonitrile, and compare the effect of solvents and deacid reagents on the region-selectivity and yield. Although the overall conversion yield doesn’t change so much among DMSO, DMF and CH3CN, the solvent of DMSO can distinctly improve the region-selectivity. The pure product of 5-amino-1-benzyl-4-cyano-pyrazole can be conveniently recrystallized from 95% ethanol with a separation yield of 62% when using DMSO and CsCO3 as reaction solvent and deacid reagent, respectively. Its chemical structure is characterized with 1H NMR and single crystal X Ray diffraction, which belongs to monoclinic space group P2(1)c with a = 1.4333 (3) nm, b = 0.6187(14) nm, c = 2.2389 (5) nm, α = 90°, β = 93.773(4)°, γ = 90°, V = 1.981.1(8) nm3, Z = 8, Dc = 1.329 g cm-3, λ = 0.71073 nm, μ (Mo Kα) = 0.085 mm-1, F (000) = 832.
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