2-hydrazino-4-tosyl-5-chloro-1,3-thiazole | 297142-57-5

• 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: 2-hydrazino-4-tosyl-5-chloro-1,3-thiazole
• 英文别名: 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole；5-Chloro-2-hydrazinyl-4-tosylthiazole；[5-chloro-4-(4-methylphenyl)sulfonyl-1,3-thiazol-2-yl]hydrazine
• CAS: 297142-57-5
• 化学式: C₁₀H₁₀ClN₃O₂S₂
• 分子量: 303.793
• InChiKey: LTYGPQBYHHRNNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  间硝基苯甲醛 、 2-hydrazino-4-tosyl-5-chloro-1,3-thiazole 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到N-[5-Chloro-4-(toluene-4-sulfonyl)-thiazol-2-yl]-N'-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-hydrazine
  参考文献：
  名称：

  摘要：

  Treatment of 1-tosyl-2,2-dichloroethenyl isothiocyanate with alcohols, thiols, primary and secondary amines, hydrazine and its derivatives, and phosphonium ylides results in addition of the O-, S-, N-, or C-nucleophilic center to the isothiocyanate, group, followed by cyclocondensation with elimination of hydrogen chloride and formation of the corresponding 2-functionally substituted 4-tosyl-5-chloro-1,3-thiazoles. Further transformations of these compounds were studied, and a series of previously unknown types of 3-functionally substituted 1,3-thiazole derivatives were prepared.

  DOI：

  10.1023/a:1023337112138
• 作为产物：
  描述：

  2,2-dichloro-1-p-tolylsulfonylethenyl isothiocyanate 在 肼 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以74%的产率得到2-hydrazino-4-tosyl-5-chloro-1,3-thiazole
  参考文献：
  名称：

  摘要：

  Treatment of 1-tosyl-2,2-dichloroethenyl isothiocyanate with alcohols, thiols, primary and secondary amines, hydrazine and its derivatives, and phosphonium ylides results in addition of the O-, S-, N-, or C-nucleophilic center to the isothiocyanate, group, followed by cyclocondensation with elimination of hydrogen chloride and formation of the corresponding 2-functionally substituted 4-tosyl-5-chloro-1,3-thiazoles. Further transformations of these compounds were studied, and a series of previously unknown types of 3-functionally substituted 1,3-thiazole derivatives were prepared.

  DOI：

  10.1023/a:1023337112138

文献信息

• Transformations of 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole
  作者：K. V. Turov、T. K. Vinogradova、B. S. Drach

  DOI：10.1134/s1070363208110248

  日期：2008.11

  Accessible 2,2-dichloro-1-p-tolylsulfonylethenyl isothiocyanate reacted with hydrazine hydrate to give 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole whose reactions with thiols and amines followed a complicated pattern. Treatment of 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole with acetylacetone led to the formation of previously unknown 5-chloro-2-(3,5-dimethyl-1H-pyrazol-1-yl)-4-p-tolylsulfonyl-1,3-thiazole which reacted with O-, S-, and N-centered nucleophiles at the C(5) atom with high regioselectivity.