4-(Dimethylamino)-2-(methylthio)-3-isopropyl-5-(isopropylamino)thiazolium chloride

• 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-(Dimethylamino)-2-(methylthio)-3-isopropyl-5-(isopropylamino)thiazolium chloride
• 英文别名: 4-N,4-N-dimethyl-2-methylsulfanyl-5-N,3-di(propan-2-yl)-1,3-thiazol-3-ium-4,5-diamine;chloride
• 化学式: C₁₂H₂₄N₃S₂*Cl
• 分子量: 309.928
• InChiKey: AQAKEQCPPWHVQW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  19.15
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(Dimethylamino)-2-(methylthio)-3-isopropyl-5-(isopropylamino)thiazolium chloride 以 甲苯 为溶剂， 反应 1.0h， 以48%的产率得到4-(Dimethylamino)-3-isopropyl-5-(isopropylimino)-2-thioxothiazolidine
  参考文献：
  名称：

  Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates

  摘要：

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.

  DOI：

  10.1021/jo00074a032
• 作为产物：
  描述：

  N,N-二甲基硫代甲酰胺 、 异氰化异丙酯 、 Carbonochloridimidothioic acid, (1-methylethyl)-, methyl ester 以 四氢呋喃 为溶剂， 反应 2.0h， 以55%的产率得到4-(Dimethylamino)-2-(methylthio)-3-isopropyl-5-(isopropylamino)thiazolium chloride
  参考文献：
  名称：

  Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates

  摘要：

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.

  DOI：

  10.1021/jo00074a032