6-chloro-5-(2,3-dichlorophenoxy)-1-methyl-2-methylthio-1H-benzimidazole | 145770-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chloro-5-(2,3-dichlorophenoxy)-1-methyl-2-methylthio-1H-benzimidazole
• 英文别名: N3-Methyltriclabendazole；6-chloro-5-(2,3-dichlorophenoxy)-1-methyl-2-methylsulfanylbenzimidazole
• CAS: 145770-89-4
• 化学式: C₁₅H₁₁Cl₃N₂OS
• 分子量: 373.69
• InChiKey: ZWTBJNLMGQSDDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.8±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三氯苯哒唑 、 碘甲烷 在 AG-MP₁ anion exchange resin 作用下， 以 二氧化碳 为溶剂， 80.0 ℃ 、20.0 MPa 条件下， 反应 0.33h， 生成 6-chloro-5-(2,3-dichlorophenoxy)-1-methyl-2-methylthio-1H-benzimidazole
  参考文献：
  名称：

  Simultaneous Extraction and Methylation of Acidic Analytes Adsorbed onto Ion Exchange Resins Using Supercritical Carbon Dioxide Containing Methyl Iodide

  摘要：

  Methylation of a wide range of organic acids with methyl iodide was simply and efficiently performed on anion exchange resins with either supercritical carbon dioxide or acetonitrile as solvents. Analytes including chlorophenoxyacetic acids, pentachlorophenol, and quinoxaline-2-carboxylic acid were displaced from the resin in a single step as their methyl esters or ethers in high yield using the supercritical fluid extraction (SFE) system, The conversion of 2,4-D and 2,4,5-T (solutions of 100 and 35 ppb, respectively) to their methyl esters was complete in 30 min and gave yields of 92% and 99% with coefficients of variation of 10%. Analytes in up to 200 mt of aqueous solution could be trapped on 0.1 g of AG MP-1 anion exchange resin and derivatized and eluted using methyl iodide in supercritical carbon dioxide at 200 bar and 80 degrees C, Less acidic compounds including albendazole, fenbendazole, triclabendazole, and sulfadimidine could also be derivatized on the resin under SFE conditions or in a quick and inexpensive procedure using acetonitrile; however, these compounds gave lower yields and multiple methylated products.

  DOI：

  10.1021/ac00101a023

文献信息

• Iddon, Brian, Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 9, p. 673 - 701
  作者：Iddon, Brian

  DOI：——

  日期：——
• 2H-benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles
  作者：Brian Iddon、Peter Kutschy、Andrew G. Robinson、Hans Suschitzky、Walter Kramer、Franz A. Neugebauer

  DOI：10.1039/p19920003129

  日期：——

  A new synthesis of the selective anthelmintic agent triclabendazole 7 from the readily available 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 2 by simple steps is described. Analogous benzimidazoles difficult to prepare by conventional methods are similarly obtained. Triclabendazole can exist as a low-melting metastable solid (m.p. 85-90-degrees-C) convertible by heating or recrystallisation from ethanol into its stable form (m.p. 1 76-1 78-degrees-C).
• Simultaneous Extraction and Methylation of Acidic Analytes Adsorbed onto Ion Exchange Resins Using Supercritical Carbon Dioxide Containing Methyl Iodide
  作者：S. N. Chatfield、M. Y. Croft、T. Dang、E. J. Murby、G. Y. F. Yu、R. J. Wells

  DOI：10.1021/ac00101a023

  日期：1995.3.1

  Methylation of a wide range of organic acids with methyl iodide was simply and efficiently performed on anion exchange resins with either supercritical carbon dioxide or acetonitrile as solvents. Analytes including chlorophenoxyacetic acids, pentachlorophenol, and quinoxaline-2-carboxylic acid were displaced from the resin in a single step as their methyl esters or ethers in high yield using the supercritical fluid extraction (SFE) system, The conversion of 2,4-D and 2,4,5-T (solutions of 100 and 35 ppb, respectively) to their methyl esters was complete in 30 min and gave yields of 92% and 99% with coefficients of variation of 10%. Analytes in up to 200 mt of aqueous solution could be trapped on 0.1 g of AG MP-1 anion exchange resin and derivatized and eluted using methyl iodide in supercritical carbon dioxide at 200 bar and 80 degrees C, Less acidic compounds including albendazole, fenbendazole, triclabendazole, and sulfadimidine could also be derivatized on the resin under SFE conditions or in a quick and inexpensive procedure using acetonitrile; however, these compounds gave lower yields and multiple methylated products.