6-chloro-N,N'-bis(2,4-dimethylphenyl)-[1,3,5]triazine-2,4-diamine | 374101-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-chloro-N,N'-bis(2,4-dimethylphenyl)-[1,3,5]triazine-2,4-diamine
• 英文别名: 6-chloro-N,N'-bis(2,4-dimethylphenyl)-1,3,5-triazine-2,4-diamine；6-chloro-2-N,4-N-bis(2,4-dimethylphenyl)-1,3,5-triazine-2,4-diamine
• CAS: 374101-00-5
• 化学式: C₁₉H₂₀ClN₅
• mdl: MFCD01952265
• 分子量: 353.854
• InChiKey: RWBGEFYTMUJWHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydrazino-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile 、 6-chloro-N,N'-bis(2,4-dimethylphenyl)-[1,3,5]triazine-2,4-diamine 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以42%的产率得到2-{N'-[4,6-Bis-(2,4-dimethyl-phenylamino)-[1,3,5]triazin-2-yl]-hydrazino}-1-methyl-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of some new 3,4-dihydropyrimidin-4-ones

  摘要：

  Condensation of 5-cyano-2-hydrazino-3-N-methyl-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4-one (3a and 3b) with 2 4-bisalkyl/arylamino-6-chloro-s-triazine (4) gave the corresponding 2,4-bisalkyl/arylamino-6-[5'-cyano-3'-N-methyl]-6'-phenyl/p-chlorophenyl-3',4'-dihydropyrimidin-4'-one-2'-yl-hydrazino-s-triazines (5a-n and 6a-n). The compounds 4 have been prepared by the condensation of cyanuric chloride and different alkyl/aryl amines. The reaction between 5-cyano-3-N-methyl-2-methylthio-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4-one (2a and 2b) with hydrazine hydrate furnished 3a and 3b, respectively. The condensation of 6-phenyl/p-chlorophenyl/5-cyano-2-mercapto-3,4-dihydropyrimidin-4-one (1a and 1b) with methyl iodide yielded 2a and 2b, respectively. All the products have been evaluated in vitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37 Rv. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01118-1
• 作为产物：
  描述：

  三聚氯氰 、 2,4-二甲基苯胺 在 sodium acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 以95%的产率得到6-chloro-N,N'-bis(2,4-dimethylphenyl)-[1,3,5]triazine-2,4-diamine
  参考文献：
  名称：

  使用乙酸作为溶剂的氰尿酰氯芳基胺化的高效“绿色”方法

  摘要：

  乙酸是一种廉价，环保的溶剂，可用于氰尿酰氯与包括硝基苯胺在内的芳香胺的简便，清洁和高收率的芳基胺化。与以前报道的方法相比，大大简化了乙酸介质中的芳基胺化反应和分离步骤。在适当条件下，可以以受控方式连接相同或不同的苯胺残基，从而分别以优异的产率获得对称和不对称的1,3,5-三嗪衍生物。

  DOI：

  10.1002/jhet.5570450236

文献信息

• An efficient, “green” approach to aryl amination of cyanuric chloride using acetic acid as solvent
  作者：Kirill A. Kolmakov

  DOI：10.1002/jhet.5570450236

  日期：2008.3

  Acetic acid is an inexpensive and environmentally friendly solvent for facile, clean and high-yielding aryl amination of cyanuric chloride with aromatic amines, including nitroanilines. Aryl amination in acetic acid medium and isolation protocol are greatly simplified as compared to previously reported procedures. Under proper conditions, it is possible to attach the same or different aniline residues

  乙酸是一种廉价，环保的溶剂，可用于氰尿酰氯与包括硝基苯胺在内的芳香胺的简便，清洁和高收率的芳基胺化。与以前报道的方法相比，大大简化了乙酸介质中的芳基胺化反应和分离步骤。在适当条件下，可以以受控方式连接相同或不同的苯胺残基，从而分别以优异的产率获得对称和不对称的1,3,5-三嗪衍生物。
• Synthesis and biological evaluation of some new 3,4-dihydropyrimidin-4-ones
  作者：Jayesh Modha、Neela Datta、Hansa Parekh

  DOI：10.1016/s0014-827x(01)01118-1

  日期：2001.8

  Condensation of 5-cyano-2-hydrazino-3-N-methyl-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4-one (3a and 3b) with 2 4-bisalkyl/arylamino-6-chloro-s-triazine (4) gave the corresponding 2,4-bisalkyl/arylamino-6-[5'-cyano-3'-N-methyl]-6'-phenyl/p-chlorophenyl-3',4'-dihydropyrimidin-4'-one-2'-yl-hydrazino-s-triazines (5a-n and 6a-n). The compounds 4 have been prepared by the condensation of cyanuric chloride and different alkyl/aryl amines. The reaction between 5-cyano-3-N-methyl-2-methylthio-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4-one (2a and 2b) with hydrazine hydrate furnished 3a and 3b, respectively. The condensation of 6-phenyl/p-chlorophenyl/5-cyano-2-mercapto-3,4-dihydropyrimidin-4-one (1a and 1b) with methyl iodide yielded 2a and 2b, respectively. All the products have been evaluated in vitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37 Rv. (C) 2001 Elsevier Science S.A. All rights reserved.