N-[6-(thiophen-2-yl)-4-(trifluoromethyl)pyrimidin-2-yl]-1H-benzo[d]imidazol-2-amine

• 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: N-[6-(thiophen-2-yl)-4-(trifluoromethyl)pyrimidin-2-yl]-1H-benzo[d]imidazol-2-amine
• 英文别名: N-[4-(2-thienyl)-6-(trifluoromethyl)-2-pyrimidinyl]-1H-benzimidazol-2-amine；N-[4-thiophen-2-yl-6-(trifluoromethyl)pyrimidin-2-yl]-1H-benzimidazol-2-amine
• 化学式: C₁₆H₁₀F₃N₅S
• 分子量: 361.35
• InChiKey: MKFZIXSPXSZSBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-胍基苯并咪唑 、 alkaline earth salt of/the/ methylsulfuric acid 以 水 为溶剂， 反应 8.0h， 以77%的产率得到N-[6-(thiophen-2-yl)-4-(trifluoromethyl)pyrimidin-2-yl]-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Efficient synthetic access to novel N-(Pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines in an aqueous medium

  摘要：

  This study describes a simple, efficient, and environmentally benign procedure for synthesizing a novel series of 13 N-(pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines, from the cyclocondensation reaction of (benzo[d]imidazolyl)guanidine with 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones or 2,2,2-trifluoro-1-(2-methoxycyclohexen-1-en-1-yl)ethanone. The (benzo[d]imidazolyl)guanidine precursor was earlier obtained from the reactions of cyanoguanidine with o-phenylenediamine. The trifluoroacetylated enol ethers were synthesized from the trifluoroacetylation reaction of enol ethers or acetals with trifluoroacetic anhydride. The main reactions were performed in pure refluxing water as the solvent (1-24 h), without catalysts, and the corresponding new N-(pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines were obtained at good to excellent yields (60-90 %). Subsequently, N-alkylation reactions were performed to obtain tertiary amines and to increase the solubility of the amines.[GRAPHICS].

  DOI：

  10.1007/s00706-015-1524-6