4,5-dichloroisothiazole-3-carboxamide | 681854-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dichloroisothiazole-3-carboxamide
• 英文别名: 4,5-dichloro-1,2-thiazole-3-carboxamide
• CAS: 681854-77-3
• 化学式: C₄H₂Cl₂N₂OS
• mdl: MFCD03766587
• 分子量: 197.045
• InChiKey: IVSPEDPJSQZQOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dichloroisothiazole-3-carboxamide 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 以78%的产率得到4,5-dichloro-1,2-thiazol-3-amine
  参考文献：
  名称：

  3-氨基-4,5-二氯异噻唑的合成

  摘要：

  从可及的4,5-二氯-1,2-噻唑-3-羰基叠氮化物和-3-羧酰胺分别经Curtius和Hofmann重排合成4,5-二氯-1,2-噻唑-3-胺。从制备的观点来看，发现涉及库尔修斯重排的方法是更有利的。

  DOI：

  10.1134/s1070428009040149
• 作为产物：
  描述：

  4,5-dichloroisothiazole-3-carbonyl chloride 在 ammonium hydroxide 作用下， 反应 4.0h， 以87%的产率得到4,5-dichloroisothiazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of 4,5-Dichloroisothiazole-3-carboxylic Acid Amides and Esters

  摘要：

  Previously unknown 4,5-dichloroisothiazole-3-carboxylic acid amides and esters were synthesized by reactions of 4,5-dichloroisothiazole-3-carbonyl chloride with ammonia, heterocyclic and aromatic amines, and functionally substituted alcohols and phenols.

  DOI：

  10.1023/b:rujo.0000045195.47004.a9

文献信息

• Synthesis of 4,5-dichloro-3-cyanoisothiazole and its functional derivatives
  作者：V. I. Potkin、Yu. S. Zubenko、N. I. Nechai、A. I. Bykhovets、P. V. Kurman

  DOI：10.1134/s1070428008070154

  日期：2008.7

  By treating with phosphorus pentoxide the 4,5-dichloroisothiazole-3-carboxamide 4,5-dichloro-3-cyanoisothiazole was synthesized whose reactions with piperidine, phenyl- and benzylthiols occurred with replacement of the chlorine atom in the position 5 by the residue of the corresponding nucleophile. Reactions with sodium thiobytylate and also with sodium methylate in methanol led to the formation both of the products of chlorine substitution by BuS or MeO groups respectively and of addition products of methanol to the cyano group. The reaction of butanethiol with cyanoisothiazole in 2-propanol in the presence of sodium 2-propylate was more selective and resulted in the replacement of the chlorine atom in the position 5 by the residue of the butanethiol.