5-[4-Chloro-[1,2,3]dithiazol-(5Z)-ylideneamino]-[1,3,4]thiadiazole-2-carbonitrile | 488713-06-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-[4-Chloro-[1,2,3]dithiazol-(5Z)-ylideneamino]-[1,3,4]thiadiazole-2-carbonitrile
• 英文别名: 5-[(Z)-(4-chlorodithiazol-5-ylidene)amino]-1,3,4-thiadiazole-2-carbonitrile
• CAS: 488713-06-0
• 化学式: C₅ClN₅S₃
• 分子量: 261.74
• InChiKey: FXURRFYDELSYGO-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[4-Chloro-[1,2,3]dithiazol-(5Z)-ylideneamino]-[1,3,4]thiadiazole-2-carbonitrile 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到N-(5-Cyano-[1,3,4]thiadiazol-2-yl)-2-nitrilo-thioacetamide
  参考文献：
  名称：

  From tetrazoles via hydrazonoyl chlorides to 1,3,4-thiadiazole oligomers

  摘要：

  5-Substituted tetrazoles react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides (14) in high yield. 5-Aminotetrazole reacts further to give an extended bis-imine (6) which, with triphenylphosphine at room temperature, rapidly gives 1,3,4-thiadiazoles 15 and 17. The mono-imines 14 react similarly to give simpler thiadiazoles 18 in high yield. By repetition of the tetrazole formation and Appel salt-triphenylphosphine sequence, these 2-cyanothiadiazoles 18 are converted in high yield into thiadiazole dimers and trimers 21, n=1 and 2. These reactions are explained mechanistically. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01505-7
• 作为产物：
  描述：

  在 二甲基亚砜 作用下， 反应 4.0h， 以25%的产率得到5-[4-Chloro-[1,2,3]dithiazol-(5Z)-ylideneamino]-[1,3,4]thiadiazole-2-carbonitrile
  参考文献：
  名称：

  From tetrazoles via hydrazonoyl chlorides to 1,3,4-thiadiazole oligomers

  摘要：

  5-Substituted tetrazoles react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides (14) in high yield. 5-Aminotetrazole reacts further to give an extended bis-imine (6) which, with triphenylphosphine at room temperature, rapidly gives 1,3,4-thiadiazoles 15 and 17. The mono-imines 14 react similarly to give simpler thiadiazoles 18 in high yield. By repetition of the tetrazole formation and Appel salt-triphenylphosphine sequence, these 2-cyanothiadiazoles 18 are converted in high yield into thiadiazole dimers and trimers 21, n=1 and 2. These reactions are explained mechanistically. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01505-7

文献信息

• Conversion of tetrazoles into hydrazonoyl chlorides. Novel donor–dithiazolium interactions
  作者：Charles W. Rees、Sivaprasad Sivadasan、Andrew J. P. White、David J. Williams

  DOI：10.1039/b202211g

  日期：2002.6.27

  5-Substituted tetrazoles 13, readily prepared from RCN and aluminium azide, react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides 16 in high yield. 5-Aminotetrazole 4 reacts further to give the extended bis(iminodithiazole) 6 and a minor product 7. Mechanisms are proposed for these reactions (except for the formation of 7) which are supported by the smooth conversion of

  5位替补 四唑 13，由RCN和叠氮化铝在室温下，与Appel盐1迅速反应，以高收率得到酰氯16。5-氨基四唑4进一步反应，得到延伸的双（亚氨基二噻唑）6和次要产物7。提出了这些反应的机理（除了7的形成以外），这些机理由5-氨基-2-取代基的平滑转化得到支持。四唑 11，但不被5-氨基-1-取代四唑，分为正常的亚氨基二噻唑类。12。红色的双（亚胺）6在温暖的条件下重排为黄色的1,3,4-噻二唑19二甲基亚砜。的结构1，6，7和19被证明X射线晶体学 这也表明在每种情况下，相邻的二噻唑环硫原子与任一氧之间都存在很强的3中心分子间相互作用， 氮 或氯供体。