N-(5-氯-1,3,4-噻二唑-2-基)乙酰胺 | 60320-32-3

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(5-氯-1,3,4-噻二唑-2-基)乙酰胺
• 中文别名: 乙酰唑胺杂质
• 英文名称: 2-acetamido-5-chloro-1,3,4-thiadiazole
• 英文别名: N-(5-chloro-1,3,4-thiadiazol-2-yl)acetamide
• CAS: 60320-32-3
• 化学式: C₄H₄ClN₃OS
• mdl: MFCD00723607
• 分子量: 177.614
• InChiKey: CKUUONNLVFAZNC-UHFFFAOYSA-N

物化性质

• 熔点：
  245-246 °C(Solv: ethanol (64-17-5))
• 密度：
  1.608±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

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：
  0.25
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331

反应信息

• 作为反应物：
  描述：

  N-(5-氯-1,3,4-噻二唑-2-基)乙酰胺 、 3,4,5-三甲氧基苄醇 在 potassium tert-butylate 作用下， 以 乙二醇二甲醚 为溶剂， 以52%的产率得到N-[5-(3,4,5-Trimethoxy-benzyloxy)-[1,3,4]thiadiazol-2-yl]-acetamide
  参考文献：
  名称：

  酰胺阴离子作为亲核杂芳族取代中的意外活化基团

  摘要：

  与中性酰胺基和氨基取代基相比，乙酰氨基阴离子取代基意外地在哒嗪，酞嗪，噻唑和噻二唑中用醇盐进行卤化物的亲核置换。

  DOI：

  10.1016/0040-4039(96)00734-4
• 作为产物：
  描述：

  2-乙酰氨基-5-巯基-1,3,4-噻二唑 在 盐酸 、 双氧水 、 溶剂黄146 作用下， 反应 8.0h， 以53%的产率得到N-(5-氯-1,3,4-噻二唑-2-基)乙酰胺
  参考文献：
  名称：

  GIAO/DFT ¹³C NMR Chemical Shifts of 1,3,4-Thiadiazoles

  摘要：

  H-1, C-13 and N-15 NMR spectra of 2-acetylamino-1,3,4-thiadiazole and its 5-substituted derivatives have been measured and assigned based on reference data, as well as homo- and heteronuclear 2 D NMR experiments. In addition, the GIAO/DFT approach at the B3LYP level of theory using the 6-311G basis set was used to calculate the C-13 NMR chemical shifts. Although this method gives reliable results for 2-arylhydrazones of 1,3-diphenylpropanetrione, 2-phenacylpyridines, (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines, 4-fluoroanilines, (1Z,3Z)-1,4-di(pyridin-2-yl)buta-1,3-dienediols and their tautomeric forms, the calculated chemical shifts for the 1,3,4-thiadiazoles studied are less satisfactory. Presence of the sulfur atom(s) seems to be responsible for such behavior.

  DOI：

  10.1080/10426500701407755

文献信息

• Syntheses of arylsulfonyl-1,3,4-thiadiazoles
  作者：A. Shafiee、A. Foroumadi

  DOI：10.1002/jhet.5570330610

  日期：1996.11

  Reaction of sodium arylsulfinate with 2-aryl-5-chloro-1,3,4-thiadiazole gave 2-aryl-5-arylsulfonyl-1,3,4-thiadiazole (3) in good yield. Starting from readily available 2-amino-5-benzylmercapto-1,3,4-thiadiazole compound 7 was obtained in three steps in moderate yield. Reaction of compound 7 with sodium arylsulfinate afforded 2,5-diarylsulfonyl-1,3,4-thiadiazole (11). Oxidation of compound 10 with hydrogen

  芳基亚磺酸钠与2-芳基-5-氯-1,3,4-噻二唑的反应以良好的收率得到2-芳基-5-芳基磺酰基-1,3,4-噻二唑（3）。从容易开始的2-氨基-5- benzylmercapto -1,3,4-噻二唑化合物7在适中的产率三个步骤而获得。化合物7与芳基亚磺酸钠反应，得到2,5-二芳基磺酰基-1,3,4-噻二唑（11）。用过氧化氢在乙酸中氧化化合物10，以高收率得到2-芳基磺酰基-5-苄基磺酰基I-1,3,4-噻二唑（12）。
• Russo; Santagati; Santagati, Farmaco, Edizione Scientifica, 1979, vol. 34, # 8, p. 688 - 697
  作者：Russo、Santagati、Santagati

  DOI：——

  日期：——
• Akerblom,E.; Skagius,K., Acta Chemica Scandinavica (1947), 1964, vol. 18, # 1, p. 174 - 184
  作者：Akerblom,E.、Skagius,K.

  DOI：——

  日期：——
• GIAO/DFT ¹³C NMR Chemical Shifts of 1,3,4-Thiadiazoles
  作者：Hossein Loghmani-Khouzani、Teresa Rauckyte、Borys Ośmiałowski、Ryszard Gawinecki、Erkki Kolehmainen

  DOI：10.1080/10426500701407755

  日期：2007.7.19

  H-1, C-13 and N-15 NMR spectra of 2-acetylamino-1,3,4-thiadiazole and its 5-substituted derivatives have been measured and assigned based on reference data, as well as homo- and heteronuclear 2 D NMR experiments. In addition, the GIAO/DFT approach at the B3LYP level of theory using the 6-311G basis set was used to calculate the C-13 NMR chemical shifts. Although this method gives reliable results for 2-arylhydrazones of 1,3-diphenylpropanetrione, 2-phenacylpyridines, (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines, 4-fluoroanilines, (1Z,3Z)-1,4-di(pyridin-2-yl)buta-1,3-dienediols and their tautomeric forms, the calculated chemical shifts for the 1,3,4-thiadiazoles studied are less satisfactory. Presence of the sulfur atom(s) seems to be responsible for such behavior.
• Amide anions as unexpected activating groups in nucleophilic heteroaromatic substitution
  作者：Iain Gillies、Charles W. Rees

  DOI：10.1016/0040-4039(96)00734-4

  日期：1996.6

  Nucleophilic displacement of halide by alkoxide in pyridazines, phthalazines, a thiazole and a thiadiazole is unexpectedly activated by acetamido anion substituents compared to neutral amido and amino substituents.

  与中性酰胺基和氨基取代基相比，乙酰氨基阴离子取代基意外地在哒嗪，酞嗪，噻唑和噻二唑中用醇盐进行卤化物的亲核置换。