N'-(4-bromophenyl)propanimidamide

• 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'-(4-bromophenyl)propanimidamide
• 化学式: C₉H₁₁BrN₂
• 分子量: 227.104
• InChiKey: JJFYIQVVKSJWGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N'-(4-bromophenyl)propanimidamide 在 三氯化硼 、 水 作用下， 以 甲苯 为溶剂， 反应 4.5h， 以55%的产率得到7-bromo-3-ethyl-1,2-dihydro-1-hydroxy-2,4-benzodiaza-1-borine mono hydrochloride
  参考文献：
  名称：

  A facile synthesis of 2,4-diaza-1-borines from anilines

  摘要：

  A general synthesis of diazaborines is described with the in situ preparation of amidines from anilines using a nitrile and AlCl3, followed by the addition of BCl3 and heating. The diazaborines were isolated as hydrochlorides in pure form and, in the case of 5, the structure was confirmed by an X-ray analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00365-9
• 作为产物：
  描述：

  4-溴苯胺 、 丙腈 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 0.08h， 以100%的产率得到N'-(4-bromophenyl)propanimidamide
  参考文献：
  名称：

  Design of New Reaction Conditions for the Sugasawa Reaction Based on Mechanistic Insights

  摘要：

  A process to prepare 2-propionyl-4-bromoaniline by ortho acylation of 4-bromoaniline under Sugasawa conditions was developed. Upon scale-up in a pilot plant, the process gave lower yields than in the laboratory in four out of five plant runs. Analysis of the pilot-plant data, in conjunction with reaction calorimetric experiments, showed that expulsion of HCl from the reaction medium was key for obtaining high product yields. New reaction conditions were subsequently developed for carrying out ortho acylation of 4-bromoaniline (1). The reaction mixture containing aniline/BCl3/AlCl3/C2H5CN was added to a refluxing solution of toluene to allow for substantial HCl expulsion and thus obtain the optimum yield of the desired product. Aniline hydrochlorides were also shown to be suitable starting materials under these conditions. Mechanistic implications of these findings are discussed. The new reaction conditions significantly increased the yield.

  DOI：

  10.1021/op0340659

文献信息

• Design of New Reaction Conditions for the Sugasawa Reaction Based on Mechanistic Insights
  作者：Kapa Prasad、George T. Lee、Apurva Chaudhary、Michael J. Girgis、James W. Streemke、Oljan Repič

  DOI：10.1021/op0340659

  日期：2003.9.1

  A process to prepare 2-propionyl-4-bromoaniline by ortho acylation of 4-bromoaniline under Sugasawa conditions was developed. Upon scale-up in a pilot plant, the process gave lower yields than in the laboratory in four out of five plant runs. Analysis of the pilot-plant data, in conjunction with reaction calorimetric experiments, showed that expulsion of HCl from the reaction medium was key for obtaining high product yields. New reaction conditions were subsequently developed for carrying out ortho acylation of 4-bromoaniline (1). The reaction mixture containing aniline/BCl3/AlCl3/C2H5CN was added to a refluxing solution of toluene to allow for substantial HCl expulsion and thus obtain the optimum yield of the desired product. Aniline hydrochlorides were also shown to be suitable starting materials under these conditions. Mechanistic implications of these findings are discussed. The new reaction conditions significantly increased the yield.
• A facile synthesis of 2,4-diaza-1-borines from anilines
  作者：George T. Lee、Kapa Prasad、Oljan Repič

  DOI：10.1016/s0040-4039(02)00365-9

  日期：2002.4

  A general synthesis of diazaborines is described with the in situ preparation of amidines from anilines using a nitrile and AlCl3, followed by the addition of BCl3 and heating. The diazaborines were isolated as hydrochlorides in pure form and, in the case of 5, the structure was confirmed by an X-ray analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.