N-(methylsulfonyl)benzimidoyl chloride | 22354-12-7

• 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-(methylsulfonyl)benzimidoyl chloride
• 英文别名: N-methylsulfonylbenzcarboximidoyl chloride；N-(Methylsulfonyl)benzenecarboximidoyl chloride；N-methylsulfonylbenzenecarboximidoyl chloride
• CAS: 22354-12-7
• 化学式: C₈H₈ClNO₂S
• 分子量: 217.676
• InChiKey: UUGSHKAMMAISQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 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：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(methylsulfonyl)benzimidoyl chloride 在 氨 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以70%的产率得到N-methanesulfonylbenzamidine
  参考文献：
  名称：

  N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

  摘要：

  The analogues of carboxamides in which the sp(2)-hybridized oxygen atom is replaced by more electron-withdrawing groups, =NSO(2)CF(3) and =NSO(2)C(4)F(9), have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC(=NSO(2)R(f))NH(2) (Rf = CF(3), C(4)F(9)) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN=C=NSO(2)R(f) under the action of (diacyloxy-iodo)arenes. Rearrangement of related compounds ArC(=NSO(2)R)NH(2) (R = CH(3), Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.03.001
• 作为产物：
  描述：

  N-(methylsulfonyl)benzamide 在 五氯化磷 作用下， 以 氯苯 为溶剂， 反应 1.0h， 生成 N-(methylsulfonyl)benzimidoyl chloride
  参考文献：
  名称：

  WO2008/24303

  摘要：

  公开号：

文献信息

• The aza Arndt–Eistert reaction based on N-trifluoromethylsulfonylarenecarboximidoyl chlorides
  作者：Lev M. Yagupolskii、Irina I. Maletina、Liubov V. Sokolenko、Yurii G. Vlasenko、Maria V. Drozdova、Vitaliy V. Polovinko

  DOI：10.1016/j.jfluchem.2009.10.019

  日期：2010.2

  The aza analogues of carboxylic acids chlorides containing the =NSO2CF3 and =NSO2CH3 groups instead of oxygen atom were used in the Arndt-Eistert reaction. It was found that N-trifluoromethylsulfonyl-(4-fluorophenyl)-carboximidoyl chloride 1 reacts with diazomethane vigorously even at -70 degrees C with formation of 1-trifluoromethylsulfonylamino-2-(4-fluorophenyl)-2,3-dimorpholine-4-yl-propane 3, 2-trifluoromethylsulfonylamino-2-(4-fluorobenzyl)-7-oxa-4-azonia-spiro[3.5]nonane 4, 2-trifluoromethylsulfonylamino-2-(4-fluorobenzyl)-1,3-dimorpholine-4-yl-propane 5 and 1-trifluoromethyisulfonylamino-2-(4-fluorobenzyl)-2,3-dimorpholine-4-yl-propane 6. Reaction of N-methylsulfonylbenzcarboximidoyl chloride 8 with diazomethane proceeds at -15 degrees C yielding 4-chloro-4-methylsulfonylaminomethyl-3-phenyl-4,5-dihydro-1H-pyrazoline 9. (C) 2009 Elsevier B.V. All rights reserved.
• N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement
  作者：Lev M. Yagupolskii、Irina I. Maletina、Liubov V. Sokolenko、Yurii G. Vlasenko、Sergey A. Buth

  DOI：10.1016/j.jfluchem.2008.03.001

  日期：2008.6

  The analogues of carboxamides in which the sp(2)-hybridized oxygen atom is replaced by more electron-withdrawing groups, =NSO(2)CF(3) and =NSO(2)C(4)F(9), have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC(=NSO(2)R(f))NH(2) (Rf = CF(3), C(4)F(9)) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN=C=NSO(2)R(f) under the action of (diacyloxy-iodo)arenes. Rearrangement of related compounds ArC(=NSO(2)R)NH(2) (R = CH(3), Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R. (C) 2008 Elsevier B.V. All rights reserved.
• WO2008/24303
  申请人：——

  公开号：——

  公开（公告）日：——