N'-chloro-N-phenylethanimidamide | 61253-73-4

• 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'-chloro-N-phenylethanimidamide
• CAS: 61253-73-4
• 化学式: C₈H₉ClN₂
• 分子量: 168.626
• InChiKey: IVFFPQPMUDDXJN-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C(Solv: ligroine (8032-32-4))
• 沸点：
  241.6±23.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N'-chloro-N-phenylethanimidamide 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 生成 2-甲基苯并咪唑
  参考文献：
  名称：

  N-Chlorosuccinimide/Sodium Hydroxide-Mediated Synthesis of Benzimidazoles from Amidines under Mild Conditions

  摘要：

  A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.

  DOI：

  10.3987/com-12-s(n)53
• 作为产物：
  描述：

  N-phenylacetamidine 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 N'-chloro-N-phenylethanimidamide
  参考文献：
  名称：

  N-Chlorosuccinimide/Sodium Hydroxide-Mediated Synthesis of Benzimidazoles from Amidines under Mild Conditions

  摘要：

  A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.

  DOI：

  10.3987/com-12-s(n)53

文献信息

• CITERIO L.; POCAR D.; STRADI R.; GIOIA B., J. CHEM. SOC. PERKIN TRANS., PART 1, 1978, NO 4, 309-314
  作者：CITERIO L.、 POCAR D.、 STRADI R.、 GIOIA B.

  DOI：——

  日期：——
• N-Chlorosuccinimide/Sodium Hydroxide-Mediated Synthesis of Benzimidazoles from Amidines under Mild Conditions
  作者：Thanh Binh Nguyen、Ali Al-Mourabit、Ludmila Ermolenko

  DOI：10.3987/com-12-s(n)53

  日期：——

  A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.