N-(2-cyanophenyl)chloromethanimidoyl chloride | 164729-64-0

• 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-(2-cyanophenyl)chloromethanimidoyl chloride
• 英文别名: 2-(Dichloromethylideneamino)benzonitrile
• CAS: 164729-64-0
• 化学式: C₈H₄Cl₂N₂
• 分子量: 199.039
• InChiKey: SMDKRBJRVGVVSU-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  309.0±25.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-cyanophenyl)chloromethanimidoyl chloride 在 sodium sulfide 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到2-氰基苯基异氰酸酯
  参考文献：
  名称：

  Pfeiffer; Pazdera; Hetzheim, Pharmazie, 1995, vol. 50, # 1, p. 21 - 25

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基苯基异氰酸酯 在 氯 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以75%的产率得到N-(2-cyanophenyl)chloromethanimidoyl chloride
  参考文献：
  名称：

  Vibrational spectroscopic studies and ab initio calculations of 2-cyanophenylisocyanid dichloride

  摘要：

  FT-Raman and FT-IR spectra of 2-cyanophenylisocyanid dichloride were recorded and analyzed. The vibrational frequencies of the title compound have been computed using the Hartree-Fock/6-31G(*) basis and compared with the experimental values. The prepared compound was identified by NMR and mass spectra. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2006.08.045

文献信息

• Synthesis of N-(2-Cyanophenyl)chloromethanimidoyl Chloride
  作者：Pavel Pazdera、Hana Divišová、Helena Havlišová、Petr Borek

  DOI：10.3390/50200189

  日期：——

  N-(2-Cyanophenyl)chloromethanimidoyl chloride (3) was prepared from 2-isothiocyanatobenzonitrile by the reaction with sulfuryl chloride or gaseous chlorine in an inert solvent. It was found that N-(2-cyanophenyl)chloromethanimidothioic chloride (2) and bis[N-(cyanophenyl)chloromethanimidoyl] sulfide (7) are intermediates of this reaction. The chloride 3 was obtained also by a three-component one-pot

  N-(2-氰基苯基)氯甲亚胺酰氯 (3) 由 2-异硫氰酸根合苄腈通过与磺酰氯或气态氯在惰性溶剂中反应制备。发现N-(2-氰基苯基)氯甲亚氨基硫代氯化物(2)和双[N-(氰基苯基)氯甲亚胺酰基]硫化物(7)是该反应的中间体。氯化物3也是通过N-(2-氰基苯基)-甲酰胺在亚硫酰氯和磺酰氯存在下的三组分一锅反应获得的。(2-氰基苯基)-(1-[(2-氰基苯基)-亚氨基]甲氧基}亚甲基)氯化铵(6)被检测为该反应的副产物。通过GC-MS、FTIR、1H和13C NMR光谱确认所有反应产物的身份。
• One-pot Syntheses of Fused Quinazolines by Reaction of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. I. A New Synthesis of 1,3-Oxazolo- and 1,3-Oxazino[2,3-b]quinazolines
  作者：Hana Divišová、Helena Havlišová、Petr Borek、Pavel Pazdera

  DOI：10.3390/51001166

  日期：——

  12H-Benzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5a), 9-chloro-12Hbenzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5b), 2,3-dihydro-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5c), 2,3-dihydro-3,3-dimethyl-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5d) and 3,4--dihydro-2H,6H-[1,3]oxazino[2,3-b]quinazolin-6-imine (5e) were synthesized in a one-pot reaction of N-(2-cyanophenyl)chloromethanimidoyl chloride (1) with 2-aminophenols, 2-aminoethanol, and 3-aminopropanol in the presence of a base. The course of the reaction was controlled by the temperature and the amount of base used. N-(2-Cyanophenyl)-(2-hydroxyanilino)methanimidoyl chloride (3a), 2-chloro-3-(2-hydroxyphenyl)-3,4-dihydroquinazolin-4-imine (4a) and 6-imino-2H, 3H, 4H, 6H, 11H-1,3-oxazino[2,3-b]-5-quinazolinium chloride (6) were identified as intermediates of the one-pot process.

  12H-苯并[1,3]恶唑并[2,3-b]喹唑啉-12-亚胺（5a）、9-氯-12H-苯并[1,3]恶唑并[2,3-b]喹唑啉-12-亚胺（5b）、2、3-二氢-5H-[1,3]恶唑并[2,3-b]喹唑啉-5-亚胺（5c）、2,3-二氢-3,3-二甲基-5H-[1,3]恶唑并[2,3-b]喹唑啉-5-亚胺（5d）和 3、4-二氢-2H,6H-[1,3]恶唑并[2,3-b]喹唑啉-6-亚胺（5e）是由 N-(2-氰基苯基)氯甲亚胺酰氯（1）与 2-氨基苯酚、2-氨基乙醇和 3-氨基丙醇在碱存在下进行单锅反应合成的。反应过程受温度和碱用量的控制。N-(2-Cyanophenyl)-(2-hydroxyanilino)methanimidoyl chloride (3a)、2-chloro-3-(2-hydroxyphenyl)-3,4-dihydroquinazolin-4-imine (4a) 和 6-imino-2H、3H、4H、6H、11H-1,3-oxazino[2,3-b]-5-quinazolinium chloride (6) 被鉴定为一锅法的中间产物。
• Efficient synthesis of tricyclic quinazolines by one-pot cyclizations of 2-(dichloroisocyanido)benzonitrile
  作者：Anja Bodtke、Peter Langer

  DOI：10.1016/j.tetlet.2004.09.125

  日期：2004.11

  The one-pot cyclization of 2-(dichloroisocyanido)beiizonitrile with 1,4-dinucleophiles, such as alpha-aminoketones, afforded 5H-oxazolo[2,3-b]quinazolin-5-imines and related quinazolines. (C) 2004 Elsevier Ltd. All rights reserved.
• Pfeiffer; Pazdera; Hetzheim, Pharmazie, 1995, vol. 50, # 1, p. 21 - 25
  作者：Pfeiffer、Pazdera、Hetzheim、Mucke

  DOI：——

  日期：——
• Vibrational spectroscopic studies and ab initio calculations of 2-cyanophenylisocyanid dichloride
  作者：Hema Tresa Varghese、C. Yohannan Panicker、Daizy Philip、Pavel Pazdera

  DOI：10.1016/j.saa.2006.08.045

  日期：2007.7

  FT-Raman and FT-IR spectra of 2-cyanophenylisocyanid dichloride were recorded and analyzed. The vibrational frequencies of the title compound have been computed using the Hartree-Fock/6-31G(*) basis and compared with the experimental values. The prepared compound was identified by NMR and mass spectra. (C) 2006 Elsevier B.V. All rights reserved.