4-ethylamino-2-methyl-1H-benzimidazole | 1159999-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-ethylamino-2-methyl-1H-benzimidazole
• 英文别名: N-ethyl-2-methyl-1H-benzimidazol-4-amine
• CAS: 1159999-77-5
• 化学式: C₁₀H₁₃N₃
• 分子量: 175.233
• InChiKey: KIMUZJWTZOIJNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N'-二乙基-2-硝基-1,3-苯二胺 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以10%的产率得到4-ethylamino-2-methyl-1H-benzimidazole
  参考文献：
  名称：

  2,4 和 2,6-N-烷基氨基二取代和 2-N-烷基氨基取代硝基苯在弱碱性溶液中的热不稳定性：仲氨基效应

  摘要：

  我们在此报道了在无水碳酸钾存在下，通过两当量的一元胺与 2,4 或 2,6-二氟硝基苯在N , N-二甲基乙酰胺中反应制备了两类仲胺，作为生物学上重要的硝酸的前体。提供N-亚硝胺的氧化物。在这两种情况下，当反应温度保持在 130°C 以下时，这些化合物都可以定量产率制备。高于该反应温度，硝基和新形成的相邻仲胺基团之间发生意想不到的环化反应，导致低产率形成苯并咪唑或喹喔啉环。提出了环化反应的合理反应机理。

  DOI：

  10.1002/jhet.2154

文献信息

• 1,3-Bis(ethylamino)-2-nitrobenzene, 1,3-bis(<i>n</i>-octylamino)-2-nitrobenzene and 4-ethylamino-2-methyl-1<i>H</i>-benzimidazole
  作者：Christopher P. Walczak、Matthew M. Yonkey、Philip J. Squattrito、Dillip K. Mohanty、Kristin Kirschbaum

  DOI：10.1107/s0108270108008275

  日期：2008.5.15

  1,3-Bis(ethylamino)-2-nitrobenzene, C10H15N3O2, (I), and 1,3bis(n-octylamino)-2-nitrobenzene, C22H39N3O2, (II), are the first structurally characterized 1,3-bis(n-alkylamino)-2-nitrobenzenes. Both molecules are bisected though the nitro N atom and the 2-C and 5-C atoms of the ring by twofold rotation axes. Both display intramolecular N-H center dot center dot center dot O hydrogen bonds between the amine and nitro groups, but no intermolecular hydrogen bonding. The nearly planar molecules pack into flat layers ca 3.4 angstrom apart that interact by hydrophobic interactions involving the n-alkyl groups rather than by pi-pi interactions between the rings. The intra- and intermolecular interactions in these molecules are of interest in understanding the physical properties of polymers made from them. Upon heating in the presence of anhydrous potassium carbonate in dimethylacetamide, (I) and (II) cyclize with formal loss of hydrogen peroxide to form substituted benzimidazoles. Thus, 4-ethylamino-2-methyl-1H-benzimidazole, C10H13N3, (III), was obtained from (I) under these reaction conditions. Compound (III) contains two independent molecules with no imposed internal symmetry. The molecules are linked into chains via N-H center dot center dot center dot N hydrogen bonds involving the imidazole rings, while the ethylamino groups do not participate in any hydrogen bonding. This is the first reported structure of a benzimidazole derivative with 4-amino and 2-alkyl substituents.
• The Thermal Instability of 2,4 and 2,6-<i>N</i>-Alkylamino-disubstituted and 2-<i>N</i>-Alkylamino-substituted Nitrobenzenes in Weakly Alkaline Solution:<i>sec</i>-Amino Effect
  作者：Christopher Walczak、Thomas J. Payne、Colin B. Wade、Matthew Yonkey、Melissa Scheid、Alec Badour、Dilip K. Mohanty

  DOI：10.1002/jhet.2154

  日期：2015.5

  We report herein the preparation of two families of secondary amines by the reactions of two equivalents of monoamines with either 2,4 or 2,6‐difluoronitrobenzenes in N,N‐dimethylacetamide in the presence of anhydrous potassium carbonate, as precursors of biologically important nitric oxide donating N‐nitrosamines. In both instances, these compounds could be prepared in quantitative yield when the

  我们在此报道了在无水碳酸钾存在下，通过两当量的一元胺与 2,4 或 2,6-二氟硝基苯在N , N-二甲基乙酰胺中反应制备了两类仲胺，作为生物学上重要的硝酸的前体。提供N-亚硝胺的氧化物。在这两种情况下，当反应温度保持在 130°C 以下时，这些化合物都可以定量产率制备。高于该反应温度，硝基和新形成的相邻仲胺基团之间发生意想不到的环化反应，导致低产率形成苯并咪唑或喹喔啉环。提出了环化反应的合理反应机理。