2-bromo-N,N-dimethylbenzothioamide

• 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: 2-bromo-N,N-dimethylbenzothioamide
• 英文别名: N,N-dimethyl-2-bromothiobenzamide；2-bromo-N,N-dimethylbenzenecarbothioamide
• 化学式: C₉H₁₀BrNS
• 分子量: 244.155
• InChiKey: PXRXKAXKYYDXOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-N,N-dimethylbenzothioamide 以 丙酮 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Cyclometallation of N,N-dimethyl-2-bromothiobenzamide and some related thioamides with palladium(0) and palladium(II)

  摘要：

  N,N-Dimethyl-2-X-thiobenzamide [X=Cl (abbreviated as Hcbt) and Br (Hbbt)] and N,N-dimethyl-2-(2-bromophenyl) thioacetamide (Hbpt) were cyclopalladated at one of the N-methyl groups upon reaction with lithium tetrachloropalladate (II), while oxidative addition took place at the aryl-halogen bond of Hbbt, Hbpt and N,N-dimethyl-2-iodothiobenzamide (Hibt) upon reaction with bis(dibenzylideneacetone) palladium (0). The reaction products, and their tri-n-butylphosphine (PBu(3)) and 4-tert-butylpyridine (tbp) derivatives, were characterized by IR and NMR spectroscopies. All the complexes were composed of a palladathiaheterocycle with sulphur coordination of a thioamide group. The structure of (N,N-dimethylthiobenzamido) (N,N-diethyldithiocarbamato) palladium (II) was determined by X-ray analysis. There is steric hindrance between one of the N-CH3 groups and one benzene ring hydrogen atom. This should result in disfavoured benzene ring cyclopalladation of N,N-dimethylthiobenzamide (Hbt) with lithium tetrachloropalladate (II) and induce N-CH3 cyclopalladation.

  DOI：

  10.1016/0277-5387(94)00346-g
• 作为产物：
  描述：

  福美双 、 邻溴苯甲醛 在 copper(l) iodide 、 二叔丁基过氧化物 作用下， 以 乙酸乙酯 为溶剂， 以77%的产率得到2-bromo-N,N-dimethylbenzothioamide
  参考文献：
  名称：

  铜催化芳族醛与四甲基秋兰姆二硫化物合成芳基硫代酰胺

  摘要：

  § 这些作者同等贡献这项工作 专用于赫伯特·迈尔教授路德维希-马克西米利Universität大学对他的70之际个生日。 抽象的 探索了一种无需使用硫化剂即可从芳基醛和四甲基秋兰姆二硫化物（TMTD）合成芳基硫酰胺的新颖便捷的方法。在CuI和过氧化二叔丁基（DTBP）的存在下，制备了各种芳基硫代酰胺，收率良好至极佳，二硫化四甲基秋兰姆作为硫代酰胺的来源对于该转化至关重要。该协议具有广泛的底物范围，良好的收率，可操作性以及可商购的廉价原料，显示了其在有机合成中的实用合成价值。 探索了一种无需使用硫化剂即可从芳基醛和四甲基秋兰姆二硫化物（TMTD）合成芳基硫酰胺的新颖便捷的方法。在CuI和过氧化二叔丁基（DTBP）的存在下，制备了各种芳基硫代酰胺，收率良好至极佳，二硫化四甲基秋兰姆作为硫代酰胺的来源对于该转化至关重要。该协议具有广泛的底物范围，良好的收率，可操作性以及可商购的廉价原料，显示了其在有机合成中的实用合成价值。

  DOI：

  10.1055/s-0036-1590936

文献信息

• Copper-Catalyzed Synthesis of Aryl Thioamides from Aryl Aldehydes and Tetramethylthiuram Disulfide
  作者：Zhi-Bing Dong、Meng-Tian Zeng、Min Wang、Han-Ying Peng、Yu Cheng

  DOI：10.1055/s-0036-1590936

  日期：2018.2

  inexpensive raw materials, showing its practical synthetic value in organic synthesis. A novel and convenient method for the synthesis of aryl thioamides from aryl aldehydes and tetramethylthiuram disulfide (TMTD) without the use of sulfurating reagent was explored. In the presence of CuI and di-tert-butyl peroxide (DTBP), various aryl thioamides were prepared with good to excellent yields, tetramethylthiuram

  § 这些作者同等贡献这项工作 专用于赫伯特·迈尔教授路德维希-马克西米利Universität大学对他的70之际个生日。 抽象的 探索了一种无需使用硫化剂即可从芳基醛和四甲基秋兰姆二硫化物（TMTD）合成芳基硫酰胺的新颖便捷的方法。在CuI和过氧化二叔丁基（DTBP）的存在下，制备了各种芳基硫代酰胺，收率良好至极佳，二硫化四甲基秋兰姆作为硫代酰胺的来源对于该转化至关重要。该协议具有广泛的底物范围，良好的收率，可操作性以及可商购的廉价原料，显示了其在有机合成中的实用合成价值。 探索了一种无需使用硫化剂即可从芳基醛和四甲基秋兰姆二硫化物（TMTD）合成芳基硫酰胺的新颖便捷的方法。在CuI和过氧化二叔丁基（DTBP）的存在下，制备了各种芳基硫代酰胺，收率良好至极佳，二硫化四甲基秋兰姆作为硫代酰胺的来源对于该转化至关重要。该协议具有广泛的底物范围，良好的收率，可操作性以及可商购的廉价原料，显示了其在有机合成中的实用合成价值。
• Cyclometallation of N,N-dimethyl-2-bromothiobenzamide and some related thioamides with palladium(0) and palladium(II)
  作者：Matsuo Nonoyama、Kiyohiko Nakajima、Masakazu Kita

  DOI：10.1016/0277-5387(94)00346-g

  日期：1995.4

  N,N-Dimethyl-2-X-thiobenzamide [X=Cl (abbreviated as Hcbt) and Br (Hbbt)] and N,N-dimethyl-2-(2-bromophenyl) thioacetamide (Hbpt) were cyclopalladated at one of the N-methyl groups upon reaction with lithium tetrachloropalladate (II), while oxidative addition took place at the aryl-halogen bond of Hbbt, Hbpt and N,N-dimethyl-2-iodothiobenzamide (Hibt) upon reaction with bis(dibenzylideneacetone) palladium (0). The reaction products, and their tri-n-butylphosphine (PBu(3)) and 4-tert-butylpyridine (tbp) derivatives, were characterized by IR and NMR spectroscopies. All the complexes were composed of a palladathiaheterocycle with sulphur coordination of a thioamide group. The structure of (N,N-dimethylthiobenzamido) (N,N-diethyldithiocarbamato) palladium (II) was determined by X-ray analysis. There is steric hindrance between one of the N-CH3 groups and one benzene ring hydrogen atom. This should result in disfavoured benzene ring cyclopalladation of N,N-dimethylthiobenzamide (Hbt) with lithium tetrachloropalladate (II) and induce N-CH3 cyclopalladation.