N-(4-chlorophenyl)-6-methylbenzo[d]thiazol-2-amine | 85063-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-(4-chlorophenyl)-6-methylbenzo[d]thiazol-2-amine
• 英文别名: 2-(4-chloroanilino)-6-methylbenzothiazole；(4-chloro-phenyl)-(6-methyl-benzothiazol-2-yl)-amine；(4-Chlor-phenyl)-(6-methyl-benzothiazol-2-yl)-amin；p-Chlorphenylamino-6-methylbenzthiazol；N-(4-chlorophenyl)-6-methyl-1,3-benzothiazol-2-amine
• CAS: 85063-53-2
• 化学式: C₁₄H₁₁ClN₂S
• mdl: MFCD22575334
• 分子量: 274.774
• InChiKey: UKMKLZUXVXDCSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-p-Tolyl-N'-p-chlorophenyl thiourea 在 氯仿 、 溴 作用下， 生成 N-(4-chlorophenyl)-6-methylbenzo[d]thiazol-2-amine
  参考文献：
  名称：

  Studies on the Thiazoles Obtained by Direct Thiocyanogenation¹

  摘要：

  DOI：

  10.1021/ja01299a018

文献信息

• 1,10-Phenanthroline-Catalyzed Tandem Reaction of 2-Iodoanilines with Isothiocyanates in Water
  作者：Wu Zhang、Yun Yue、Dan Yu、Lei Song、Yang-Yang Xu、Yu-Jie Tian、Yu-Jun Guo

  DOI：10.1002/adsc.201200175

  日期：2012.8.13

  The 1,10-phenanthroline-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water is described, which provides an environmentally benign, efficient and simple route for the preparation of 2-aminobenzothiazoles. The present tandem process shows broad substrate scope in the absence of transition metals and phase-transfer catalysts.

  描述了2-碘苯胺与异硫氰酸酯在水中的1,10-菲咯啉催化的串联反应，这为制备2-氨基苯并噻唑提供了环境友好，有效且简单的途径。在没有过渡金属和相转移催化剂的情况下，本发明的串联方法显示出广泛的底物范围。
• A practical synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in ionic liquids
  作者：Ling Chen、Bin Huang、Quan Nie、Mingzhong Cai

  DOI：10.1002/aoc.3453

  日期：2016.6

  copper(I)‐catalyzed tandem reaction of 2‐iodoanilines with isothiocyanates was achieved in hydrophobic [bmim][PF6] ionic liquid under mild conditions, generating a variety of 2‐aminobenzothiazoles in good to excellent yields. The tandem reaction that was carried out in [bmim][PF6] has some obvious advantages such as accelerated reaction rate and increased yield as compared with the reaction run in volatile

  在疏水性[bmim] [PF 6 ]离子液体中，在温和的条件下实现了2-碘代苯胺与异硫氰酸酯的铜（I）催化串联反应，生成了各种类型的2-氨基苯并噻唑，收率高至优异。与在挥发性溶剂（例如甲苯）中进行的反应相比，在[bmim] [PF 6 ]中进行的串联反应具有一些明显的优势，例如加快了反应速度，提高了收率。此外，CuI / 1,10-菲咯啉催化体系最多可重复使用八次，而不会降低活性和效率。版权所有©2016 John Wiley＆Sons，Ltd.
• Synthesis of<i>N</i>-Substituted-2-Aminobenzothiazoles by Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of 2-Haloanilines with Isothiocyanates
  作者：Guodong Shen、Xin Lv、Weiliang Bao

  DOI：10.1002/ejoc.200900953

  日期：2009.12

  A novel and efficient formation of N-substituted-2-aminobenzothiazoles by a ligand-free copper(I)-catalyzed one-pot cascade process was developed. A variety of isothiocyanates coupled with 2-iodoanilines to give N-substituted-2-aminobenzothiazoles in moderate to excellent yields under mild conditions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  开发了一种通过无配体铜 (I) 催化的一锅级联工艺形成 N-取代-2-氨基苯并噻唑的新型有效方法。多种异硫氰酸酯与 2-碘苯胺结合，在温和条件下以中等至优异的产率得到 N-取代-2-氨基苯并噻唑。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Merrifield resin supported phenanthroline–Cu(I): a highly efficient and recyclable catalyst for the synthesis of 2-aminobenzothiazoles via the reaction of 2-haloanilines with isothiocyanates
  作者：Jin Yang、Pinhua Li、Lei Wang

  DOI：10.1016/j.tet.2011.05.121

  日期：2011.8

  recyclable catalyst in the reaction of 2-halobenzenamines with isothiocyanates for the synthesis of 2-aminobenzothiazoles. The reactions were applicable to a variety of 2-halobenzenamines and isothiocyanates, and generated the corresponding 2-aminobenzothiazoles in good yields under mild reaction conditions. Moreover, the catalyst was quantitatively recovered from the reaction mixture by a simple filtration

  一种新型的Merrifield树脂负载的菲咯啉-Cu（I）络合物已被开发出来，并用作2-卤代苯胺与异硫氰酸酯反应合成2-氨基苯并噻唑的高效可循环催化剂。该反应适用于各种2-卤代苯甲胺和异硫氰酸酯，并在温和的反应条件下以高收率产生了相应的2-氨基苯并噻唑。此外，通过简单的过滤从反应混合物中定量回收催化剂，并以几乎恒定的活性重复使用十个循环。
• A practical synthesis of 2-aminobenzothiazoles via the tandem reactions of 2-haloanilines with isothiocyanates catalyzed by immobilization of copper in MCM-41
  作者：Ruian Xiao、Wenyan Hao、Jinting Ai、Ming-Zhong Cai

  DOI：10.1016/j.jorganchem.2012.01.014

  日期：2012.5

  The heterogeneous tandem reactions of 2-haloanilines with isothiocyanates were achieved in DMSO using Et3N as base at 80 °C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(II) complex [MCM-41-2N-CuSO4], yielding a variety of 2-aminobenzothiazoles in good to excellent yields. This heterogeneous copper catalyst exhibited higher activity than CuSO4 and can be

  在3-（2-氨基乙基氨基）丙基官能化的MCM-41固定铜（II）络合物存在下，在80°C下以Et 3 N为碱，在DMSO中实现了2-卤代苯胺与异硫氰酸酯的异质串联反应[ MCM-41-2N-CuSO 4 ]，以良好至优异的产率产生各种2-氨基苯并噻唑。这种非均相铜催化剂显示出比CuSO 4高的活性，可以通过简单过滤反应溶液进行回收和再循环，并至少连续进行了10次试验，而活性没有降低。