2,4,6-trichlorosulfenamide | 17162-41-3

• 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: 2,4,6-trichlorosulfenamide
• 英文别名: 2,4,6-Trichlor-phenylsulfensaeure-amid；2,4,6-Trichlorophenyl sulfenamide；S-(2,4,6-trichlorophenyl)thiohydroxylamine
• CAS: 17162-41-3
• 化学式: C₆H₄Cl₃NS
• 分子量: 228.529
• InChiKey: ZPMGDSZFSOAHBT-UHFFFAOYSA-N

物化性质

• 沸点：
  317.4±52.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 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：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,6-trichlorosulfenamide 在 palladium on activated charcoal 硅酸四乙酯 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  一种通过芳族邻硝基硝基甲醛的席夫碱稠合嘧啶衍生物的方法。取代基对反应过程影响的研究

  摘要：

  DOI：

  10.1007/bf02297680
• 作为产物：
  描述：

  2,4,6-三氯苯硫醇 在 sodium hypochlorite 、 氨 作用下， 反应 0.5h， 生成 2,4,6-trichlorosulfenamide
  参考文献：
  名称：

  Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen:  Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

  摘要：

  A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The sigma adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkryl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of amination.

  DOI：

  10.1021/jo970582b
• 作为试剂：
  描述：

  间硝基苯腈 在 2,4,6-trichlorosulfenamide 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以21%的产率得到2-氰基-4-硝基苯胺
  参考文献：
  名称：

  Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen:  Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

  摘要：

  A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The sigma adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkryl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of amination.

  DOI：

  10.1021/jo970582b

文献信息

• Methods of making 6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form
  申请人：——

  公开号：US20040167194A1

  公开（公告）日：2004-08-26

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈在2,3,7-三氨基-4,6-二甲基-1,9-苝二羧腈和其无水单乙酸盐的情况下，可用于治疗α-2介导的疾病，如眼压高。
• [EN] METHODS OF MAKING 6-[(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)AMINO-]-7-METHYL-1H-BENZIMIDAZOLE-4-CARBONITRILE AND ITS PREFERRED SALT FORM<br/>[FR] PROCEDES DE FABRICATION DE 6-[(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)AMINO-]-7-METHYL-1H-BENZIMIDAZOLE-4-CARBONITRILE ET FORME PREFEREE D'UN SEL DE CELUI-CI
  申请人：PROCTER & GAMBLE

  公开号：WO2004074279A1

  公开（公告）日：2004-09-02

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈，基本上不含2,3,7-三氨基-4,6-二甲基-1,9-菲嗪二羧腈，以及其无水单乙酸盐，在治疗α-2介导的疾病，如眼压增高方面具有用处。
• Methods of making 6-[(4,5-dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form
  申请人：Randall Lynn Jared

  公开号：US20060122248A1

  公开（公告）日：2006-06-08

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈，基本上不含2,3,7-三氨基-4,6-二甲基-1,9-苯并二氰基的盐酸单乙酰化物，可用于治疗α-2介导的疾病，如眼压增高。
• Methods of making 6-[(4,5-Dihydro-1H-imidazol-2-yl) amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form
  申请人：The Board of Regents of the University of Nebraska

  公开号：EP1953146A1

  公开（公告）日：2008-08-06

  A method of making a compound of formula (II): comprising: a) providing a compound of formula (I): b) cyclizing the formula (I) compound in a single pot by using a non ferrous metal hydrogenation catalyst, in the presence of hydrogen or a hydrogen donor, and optionally a cyclization agent, yielding the compound of formula (II).

  一种制造式(II)化合物的方法： 包括 a) 提供式（I）化合物： b) 在氢或氢供体以及可选的环化剂存在下，使用非铁金属氢化催化剂，在一锅中环化式（I）化合物，得到式（II）化合物。
• Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen
  作者：Mieczyslaw Makosza、Maciej Bialecki

  DOI：10.1021/jo00044a002

  日期：1992.8

  Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitro-anilines.