2-(2-chlorophenyl)-2-[(4-chlorophenyl)amino]acetonitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-chlorophenyl)-2-[(4-chlorophenyl)amino]acetonitrile
• 英文别名: 2-(4-Chloroanilino)-2-(2-chlorophenyl)acetonitrile
• 化学式: C₁₄H₁₀Cl₂N₂
• mdl: MFCD12897001
• 分子量: 277.153
• InChiKey: FYCGWLJDXMHZIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)-2-[(4-chlorophenyl)amino]acetonitrile 、 N-亚磺酰苯胺 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以64%的产率得到3-(2-chlorophenyl)-4-imino-5-phenyl-2-(4-chlorophenyl)-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide
  参考文献：
  名称：

  Synthesis of 4-Imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide through Cycloaddition Reaction of N-Sulphinylanilines and N-(α-Cyano-α-aryl)-methylanilines

  摘要：

  Through the normal mode of cycloaddition reaction of N‐(α‐cyano‐α‐aryl)‐methylanilines (II) onto N‐sulphinylanilines (III) has provided 2,3,5‐triaryl‐4‐imino‐2H,3H,5H‐[1,2,5]thiadiazolidin‐1‐oxides (IV). The present protocol has advantage of convenient operation to synthesize heterocyclics in good yield.

  DOI：

  10.1002/jhet.1828
• 作为产物：
  描述：

  2-氯苯甲醛 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(2-chlorophenyl)-2-[(4-chlorophenyl)amino]acetonitrile
  参考文献：
  名称：

  Synthesis of 4-Imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide through Cycloaddition Reaction of N-Sulphinylanilines and N-(α-Cyano-α-aryl)-methylanilines

  摘要：

  Through the normal mode of cycloaddition reaction of N‐(α‐cyano‐α‐aryl)‐methylanilines (II) onto N‐sulphinylanilines (III) has provided 2,3,5‐triaryl‐4‐imino‐2H,3H,5H‐[1,2,5]thiadiazolidin‐1‐oxides (IV). The present protocol has advantage of convenient operation to synthesize heterocyclics in good yield.

  DOI：

  10.1002/jhet.1828

文献信息

• Synthesis of α-aminonitriles under mild catalytic, metal-free conditions
  作者：Baskar Nammalwar、Chelsea Fortenberry、Richard A. Bunce

  DOI：10.1016/j.tetlet.2013.11.035

  日期：2014.1

  alpha-Aminonitriles have been synthesized by a Strecker synthesis from aldehydes and ketones under mild catalytic, metal-free conditions. Aromatic aldehydes (1 equiv) were reacted with TMSCN (1 equiv) and aromatic and 1 degrees or 2 degrees aliphatic amines (1 equiv) in EtOH containing 3 mol % of NH4Cl to give high yields of alpha-aminonitriles. An alternative to adding NH4Cl as a catalyst involved the use of excess TMSCN (1.2 equiv) to promote the process. The reaction was also successful under microwave conditions using excess TMSCN with no solvent. Ketones similarly reacted with aromatic amines and excess TMSCN under conventional and microwave heating, but 30 mol % of added NH4Cl was required for optimum conversion. (C) 2013 Elsevier Ltd. All rights reserved.
• Ferric Perchlorate–Catalyzed One‐Pot Synthesis of α‐Aminonitriles using Trimethylsilylcyanide
  作者：Hossien A. Oskooie、Majid M. Heravi、Akbar Sadnia、Fatemeh Jannati、Farahnaz K. Behbahani

  DOI：10.1080/00397910701462732

  日期：2007.8
• Synthesis of 4-Imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide through Cycloaddition Reaction of N-Sulphinylanilines and N-(α-Cyano-α-aryl)-methylanilines
  作者：Manpreet Kaur、Baldev Singh

  DOI：10.1002/jhet.1828

  日期：2014.7

  Through the normal mode of cycloaddition reaction of N‐(α‐cyano‐α‐aryl)‐methylanilines (II) onto N‐sulphinylanilines (III) has provided 2,3,5‐triaryl‐4‐imino‐2H,3H,5H‐[1,2,5]thiadiazolidin‐1‐oxides (IV). The present protocol has advantage of convenient operation to synthesize heterocyclics in good yield.