1,3,4-噻二唑-2,5-二甲酰胺 | 52938-10-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,3,4-噻二唑-2,5-二甲酰胺
• 英文名称: 1,3,4-Thiadiazol-2,5-bis(carbonsaeureamid)
• 英文别名: 1,3,4-Thiadiazol-2,5-dicarbonsaeure-diamid；1,3,4-thiadiazole-2,5-dicarboxamide
• CAS: 52938-10-0
• 化学式: C₄H₄N₄O₂S
• 分子量: 172.167
• InChiKey: PBASYYFOMOXUSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,4-噻二唑-2,5-二甲酰胺 在 四磷十氧化物 作用下， 100.0 ℃ 、266.64 Pa 条件下， 生成 2,5-Dicyano-1,3,4-thiadiazol
  参考文献：
  名称：

  The preparation of dicyano-1,3,4-thiadiazole and tricyanothiazole via 1,2,3-dithiazole chemistry

  摘要：

  Treatment of 1,2-bis(4-chloro-5H-1,2,3-dithiazol-5-ylidene)hydrazine 4 with benzyltriethylaminonium iodide (1 equiv) affords dicyano-1,3,4-thiadiazole 3 and 5-cyano-1,3,4-thiadiazole-2-carboxamide 5 in 79 and 21% yields, respectively. By using polymer bound triphenylphosphine instead of benzyltriethylammonium iodide the dicyano-1,3,4-thiadiazole 3 can be isolated in 70% yield without chromatography. The reaction of DAMN with Appel salt 8 gave 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitrile 7 (14%), 2,3-bis-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)fumaronitrile 10 (14%), and 2,3-bis(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)maleonitrile 11 (24%) together with other products. The maleonitrile 11 isomerizes into the fumaronitrile 10 on irradiation at 365 nm. Reaction of aminoacetonitrile with Appel salt 8 gives the (dithiazolylidene)acetonitrile 7 in 33% yield. Treatment of (dithiazolylidene)acetonitrile 7 with polymer bound triphenylphosphine gives tricyanothiazole 6 in 76% yield. A rational general mechanism for the transformation of bisdithiazoles to percyanoheteroles is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.003
• 作为产物：
  描述：

  Dimethyl-1,3,4-thiadiazol-2,5-dicarboxylat 在 氨 作用下， 以 formamide 为溶剂， 反应 2.0h， 以87%的产率得到1,3,4-噻二唑-2,5-二甲酰胺
  参考文献：
  名称：

  Hagen, Helmut; Kohler, Rolf-Dieter; Fleig, Helmut, Liebigs Annalen der Chemie, 1980, # 8, p. 1216 - 1231

  摘要：

  DOI：

文献信息

• Thiel, W.; Mayer, R., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 4, p. 649 - 658
  作者：Thiel, W.、Mayer, R.

  DOI：——

  日期：——
• HAGEN H.; KOHLER R.-D.; FLEIG H., LIEBIGS ANN. CHEM., 1980, NO 8, 1216-1231
  作者：HAGEN H.、 KOHLER R.-D.、 FLEIG H.

  DOI：——

  日期：——
• JAUER, E. -A.;THIEL, W.;MAYER, R.;DOST, H.;MENZEL, H.
  作者：JAUER, E. -A.、THIEL, W.、MAYER, R.、DOST, H.、MENZEL, H.

  DOI：——

  日期：——
• Hagen, Helmut; Kohler, Rolf-Dieter; Fleig, Helmut, Liebigs Annalen der Chemie, 1980, # 8, p. 1216 - 1231
  作者：Hagen, Helmut、Kohler, Rolf-Dieter、Fleig, Helmut

  DOI：——

  日期：——
• The preparation of dicyano-1,3,4-thiadiazole and tricyanothiazole via 1,2,3-dithiazole chemistry
  作者：Irene C. Christoforou、Andreas S. Kalogirou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.10.003

  日期：2009.11

  Treatment of 1,2-bis(4-chloro-5H-1,2,3-dithiazol-5-ylidene)hydrazine 4 with benzyltriethylaminonium iodide (1 equiv) affords dicyano-1,3,4-thiadiazole 3 and 5-cyano-1,3,4-thiadiazole-2-carboxamide 5 in 79 and 21% yields, respectively. By using polymer bound triphenylphosphine instead of benzyltriethylammonium iodide the dicyano-1,3,4-thiadiazole 3 can be isolated in 70% yield without chromatography. The reaction of DAMN with Appel salt 8 gave 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitrile 7 (14%), 2,3-bis-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)fumaronitrile 10 (14%), and 2,3-bis(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)maleonitrile 11 (24%) together with other products. The maleonitrile 11 isomerizes into the fumaronitrile 10 on irradiation at 365 nm. Reaction of aminoacetonitrile with Appel salt 8 gives the (dithiazolylidene)acetonitrile 7 in 33% yield. Treatment of (dithiazolylidene)acetonitrile 7 with polymer bound triphenylphosphine gives tricyanothiazole 6 in 76% yield. A rational general mechanism for the transformation of bisdithiazoles to percyanoheteroles is proposed. (C) 2009 Elsevier Ltd. All rights reserved.