N,N′-(1,3,4-thiadiazole-2,5-diyl)dibenzamide | 62235-57-8

• 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,N′-(1,3,4-thiadiazole-2,5-diyl)dibenzamide
• 英文别名: 2,5-dibenzamido-1,3,4-thiadiazole；2,5-bis-benzoylamino-[1,3,4]thiadiazole；N,N'-[1,3,4]thiadiazole-2,5-diyl-bis-benzamide；N,N'-[1,3,4]Thiadiazol-2,5-diyl-bis-benzamid；2,5-Dibenzamido-1,3,4-thiadiazol；Benzamide, N,N'-1,3,4-thiadiazole-2,5-diylbis-；N-(5-benzamido-1,3,4-thiadiazol-2-yl)benzamide
• CAS: 62235-57-8
• 化学式: C₁₆H₁₂N₄O₂S
• 分子量: 324.363
• InChiKey: MGKFNHSMCHWUHE-UHFFFAOYSA-N

物化性质

• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-benzoyl-1{[(phenylformamido)methanethioyl]amino}thiourea 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到N,N′-(1,3,4-thiadiazole-2,5-diyl)dibenzamide
  参考文献：
  名称：

  Novel and Efficient Cyclization Procedure for the Synthesis of 2,5-Disubstituted-1,3,4-thiadiazoles Without Using Any Ring-Closing Reagents

  摘要：

  A novel method for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via direct ring closure of 1,6-disubstituted-2,5-dithioureas in dimethylformanide without using any ring-closing reagents has been accidentally discovered. Repeated and extended experiments confirmed that this is a very simple and efficient way to synthesize these kinds of fine chemicals. A series of novel 2,5-disubstituted-1,3,4-thiadiazoles have been synthesized via this method in good yields.

  DOI：

  10.1080/00397911.2010.548891

文献信息

• Heterocyclic compounds from urea derivatives. Part XVIII. Adducts from aminoguanidines and aroyl isothiocyanates and their cyclisation
  作者：Frederick Kurzer

  DOI：10.1039/j39700001805

  日期：——

  1-Amidino-4-benzoyl(thiosemicarbazide) hydrochloride is cyclised by hydrochloric or orthophosphoric acid to 2-amino-5-benzamido-1,3,4-thiadiazole, by acetic anhydride to the corresponding acetyl derivative, and by alkali to 3-mercapto-5-phenyl-1,2,4-triazole. 1-Amino-2-phenylguanidine salts undergo an analogous series of reactions. The mechanism of these addition–cyclisations is discussed and correlated

  等摩尔量的芳基异硫氰酸酯和氨基胍盐酸盐在甲醇水溶液中发生加成反应，可提供出色的产率的1-ami基-4-芳酰基（硫代氨基脲），可作为盐酸盐，苦味酸盐或游离碱分离。盐酸或正磷酸将1-yl基-4-苯甲酰基（硫代氨基脲）盐酸盐环化成2-氨基-5-苯甲酰胺基1,3,4-噻二唑，乙酸酐成相应的乙酰基衍生物，碱成3-巯基-5-苯基-1，2，4-三唑。1-氨基-2-苯基胍盐经历一系列类似的反应。讨论了这些加成环化的机理，并将其与类似反应的机理联系起来。
• Fromm, Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 11
  作者：Fromm

  DOI：——

  日期：——
• Fromm, Justus Liebigs Annalen der Chemie, 1926, vol. 447, p. 303
  作者：Fromm

  DOI：——

  日期：——