4-chloro-N-ethylbenzothioamide | 70262-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-ethylbenzothioamide
• 英文别名: 4-Chloro-N-ethylbenzene-1-carbothioamide；4-chloro-N-ethylbenzenecarbothioamide
• CAS: 70262-81-6
• 化学式: C₉H₁₀ClNS
• 分子量: 199.704
• InChiKey: CZUHGLIBZVWVBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-N-ethylbenzothioamide 在 正丁基锂 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.75h， 生成 5-chloro-(Z)-N-ethyl-3-phenylbenzo[c]thiophen-1(3H)-imine
  参考文献：
  名称：

  2-(1-羟烷基)苯并硫代酰胺环化合成苯并[c]噻吩-1(3H)-亚胺和2,3-二氢-1H-异吲哚-1-硫酮衍生物

  摘要：

  The reaction of N-alkyl-2,N-dilithiobenzothioamides, generated by treating N-alkylbenzothioamides with two equivalents of butyllithium, with aldehydes gives the corresponding 2-(1-hydroxyalkyl)benzothioamides, which undergo cyclization on treatment with methanesulfonyl chloride in the presence of triethylamine to yield 3,N-disubstituted (Z)-benzo[c]thiophen-1(3H)-imines. 2,3-Disubstituted 2,3-dihydro-1H-isoindole-1-thiones are obtained by the reaction of the above hydroxy thioamides with two equivalents of sodium hydride followed by an equivalent of phenyl chloroformate.

  DOI：

  10.3987/com-17-13817
• 作为产物：
  描述：

  4-氯-N-乙基苯甲酰胺 在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 以93.5%的产率得到4-chloro-N-ethylbenzothioamide
  参考文献：
  名称：

  [EN] AUTOPHAGY-INHIBITING COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS INHIBANT L'AUTOPHAGIE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2016196393A3

文献信息

• One-Pot Synthesis of (Z)-N-Substituted Isobenzofuran-1(3H)-imines from Secondary Benzothioamides and Carbonyl Compounds
  作者：Kazuhiro Kobayashi、Takashi Nogi

  DOI：10.3987/com-17-s(t)13

  日期：——

  An efficient one-pot methodology for the synthesis of (Z)-N-substituted isobenzofiiran-1(3H)-imines starting from secondary benzothioamides has been developed. The reaction of the starting materials with two equivalents of butyllithium generated 2,N-dilithio-N-alkyl(or aryl)benzothioamides, which were then allowed to react with carbonyl compounds to give, after aqueous treatment, the desired products in satisfactory yields.
• Synthesis of 3-Hydroxy-2,3-dihydro-1H-isoindole-1-thione Derivatives by the Reaction of 2,N-Dilithiobenzamides with Carboxylic Esters
  作者：Kazuhiro Kobayashi、Daiki Fujiwara、Kazuma Nozaki、Takashi Nogi

  DOI：10.3987/com-18-13946

  日期：——

  An efficient one-pot method for the preparation of 2,3-disubstituted 3-hydroxy-2,3-dihydro-1H-isoindole-1-thiones from secondary benzothioamides and carboxylic esters has been developed. Thus, the reaction of the starting thioamides with two equivalents of butyllithium generates the corresponding 2,N-dilithiobenzothioamides, which are then allowed to react with carboxylic esters to give the desired products. The similar preparation of 4- and 5-aza-analogues from 2(or 3)-bromopyridine-3(or 4)-carbothioamides, respectively, is also described.
• One-Pot Synthesis of 2-Substituted 1H-Isoindole-1,3(2H)-dithiones from Secondary Benzothioamides and Isothiocyanates
  作者：Kazuhiro Kobayashi、Daiki Fujiwara、Miyuki Tanmatsu

  DOI：10.3987/com-18-13882

  日期：——

  The reaction of 2,N-dilithiobenzothioamides, generated from readily available secondary benzothioamides and two equivalents of butyllithium, with isothiocyanates, followed by aqueous workup, gives the corresponding N-1,N-2-disubstituted benzene-1,2-dicarbothioamides, which undergo intramolecular attack of one of the thioamide nitrogen on the adjacent thiocarbonyl moiety with loss of primary amines to provide 2-substituted 1H-isoindole-1,3(2H)-dithiones.
• [EN] AUTOPHAGY-INHIBITING COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS INHIBANT L'AUTOPHAGIE ET LEURS UTILISATIONS
  申请人：PRESAGE BIOSCIENCES INC

  公开号：WO2016196393A3

  公开（公告）日：2017-05-18
• Synthesis of Benzo[c]thiophen-1(3H)-imine and 2,3-Dihydro-1H-isoindole-1-thione Derivatives through Cyclizations of 2-(1-Hydroxyalkyl)benzothioamides
  作者：Kazuhiro Kobayashi、Takashi Nogi

  DOI：10.3987/com-17-13817

  日期：——

  The reaction of N-alkyl-2,N-dilithiobenzothioamides, generated by treating N-alkylbenzothioamides with two equivalents of butyllithium, with aldehydes gives the corresponding 2-(1-hydroxyalkyl)benzothioamides, which undergo cyclization on treatment with methanesulfonyl chloride in the presence of triethylamine to yield 3,N-disubstituted (Z)-benzo[c]thiophen-1(3H)-imines. 2,3-Disubstituted 2,3-dihydro-1H-isoindole-1-thiones are obtained by the reaction of the above hydroxy thioamides with two equivalents of sodium hydride followed by an equivalent of phenyl chloroformate.