N-(2-(4-methoxyphenyl)-4-cyano-1,2,3-thiadiazol-5(2H)-ylidene)-4-chlorobenzamide

• 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: N-(2-(4-methoxyphenyl)-4-cyano-1,2,3-thiadiazol-5(2H)-ylidene)-4-chlorobenzamide
• 英文别名: 4-chloro-N-[4-cyano-2-(4-methoxyphenyl)thiadiazol-5-ylidene]benzamide
• 化学式: C₁₇H₁₁ClN₄O₂S
• 分子量: 370.819
• InChiKey: SKLHDGZTDDVTJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰氯 、 2-(4-methoxyphenyl)hydrazono-2-thiocarbamoylacetamide 以 吡啶 为溶剂， 反应 15.0h， 以70%的产率得到N-(2-(4-methoxyphenyl)-4-cyano-1,2,3-thiadiazol-5(2H)-ylidene)-4-chlorobenzamide
  参考文献：
  名称：

  Unexpected result for the acylation of arylhydrazonoethanethioamides

  摘要：

  The acylation of arylhydrazonoethanethioamides containing primary amino group did not yield acylthioamides as expected. Surprisingly, the cyclic 5-acylimino-2,5-dihydro-1,2,3-thiadiazoles were obtained. The formation of thiadiazoles in this reaction was explained by the higher ability of arylhydrazono-N-acylthioacetamide intermediates to be oxidized comparing to their precursors. The presence of pseudobicyclic aromatic structure in the reaction product was a main factor favoring the formation of 1,2,3-thiadiazole ring. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.071

文献信息

• Unexpected result for the acylation of arylhydrazonoethanethioamides
  作者：Anastasiya I. Bolgova、Kseniya I. Lugovik、Julia O. Subbotina、Pavel A. Slepukhin、Vasiliy A. Bakulev、Nataliya P. Belskaya

  DOI：10.1016/j.tet.2013.06.071

  日期：2013.9

  The acylation of arylhydrazonoethanethioamides containing primary amino group did not yield acylthioamides as expected. Surprisingly, the cyclic 5-acylimino-2,5-dihydro-1,2,3-thiadiazoles were obtained. The formation of thiadiazoles in this reaction was explained by the higher ability of arylhydrazono-N-acylthioacetamide intermediates to be oxidized comparing to their precursors. The presence of pseudobicyclic aromatic structure in the reaction product was a main factor favoring the formation of 1,2,3-thiadiazole ring. (C) 2013 Elsevier Ltd. All rights reserved.