氢氯噻嗪杂质F | 890-67-5

• 物质功能分类: 化学试剂 - 有机试剂 - 肼
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 中文名称: 氢氯噻嗪杂质F
• 英文名称: (+/-)-6-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
• 英文别名: 6-chloro-3-methyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide；6-Chlor-3-methyl-7-sulfamoyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxid；methiazide；6-chloro-3-methyl-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide
• CAS: 890-67-5
• 化学式: C₈H₁₀ClN₃O₄S₂
• 分子量: 311.77
• InChiKey: OLGOYXCALUVMCM-UHFFFAOYSA-N

物化性质

• 熔点：
  246 °C (decomp)
• 沸点：
  562.7±60.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氢氯噻嗪杂质F 以 水 、 乙腈 为溶剂， 生成 (+)-6-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
  参考文献：
  名称：

  Energy barrier determination of enantiomerization of chiral 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide type compounds by enantioselective stopped-flow HPLC

  摘要：

  The synthesis and enantioseparation of chiral 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide derivatives are reported herein. A HPLC stopped-flow procedure was applied to the determination of rate constants and free energy barriers of enantiomerization of the compounds synthesized in the presence of achiral stationary phase. The individual enantiomers of the studied compounds were isolated in parallel by preparative HPLC on a Chiraspher NT column. Rate constants and free energy barriers of enantiomerization were determined in the mobile phase. The results were used to determine the influence of the chiral stationary phase on the enantiomerization process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.035
• 作为产物：
  描述：

  5-氯-2,4-二磺酰胺基苯胺 在 Chirasphere NT column 、 硫酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 3.0h， 生成 氢氯噻嗪杂质F
  参考文献：
  名称：

  Energy barrier determination of enantiomerization of chiral 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide type compounds by enantioselective stopped-flow HPLC

  摘要：

  The synthesis and enantioseparation of chiral 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide derivatives are reported herein. A HPLC stopped-flow procedure was applied to the determination of rate constants and free energy barriers of enantiomerization of the compounds synthesized in the presence of achiral stationary phase. The individual enantiomers of the studied compounds were isolated in parallel by preparative HPLC on a Chiraspher NT column. Rate constants and free energy barriers of enantiomerization were determined in the mobile phase. The results were used to determine the influence of the chiral stationary phase on the enantiomerization process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.035

文献信息

• Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues
  作者：Jinwei Sun、Tao Tao、Dan Xu、Hui Cao、Qinggang Kong、Xinyu Wang、Yun Liu、Jianglin Zhao、Yi Wang、Yi Pan

  DOI：10.1016/j.tetlet.2018.04.054

  日期：2018.5

  A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope

  已经开发了用于合成喹唑啉酮，苯并噻二嗪和喹唑啉的通用的无金属氧化环化方法。通过该方案，一系列取代的2-氨基苯甲酰胺，2-氨基苯磺酰胺和2-（氨基甲基）苯胺与各种醇反应，从而平稳地得到所需的环状产物。该方案具有许多优点，例如底物范围广，反应条件温和，环境污染小，原子经济性高以及良率或优良率高。
• A convenient and mild cyclocondensation using water-soluble aldehydes in water
  作者：Taku Kitanosono、Soo Min Cho、Shū Kobayashi

  DOI：10.1016/j.tet.2018.10.023

  日期：2018.12

  The use of negatively charged aluminosilicate layers and Lewis acidic cations embedded therein allowed efficient cyclocondensation of bisamines with water-soluble aldehydes to be achieved in water. The protocol does not involve acidic or reflux conditions, thereby avoiding undesired byproduct formation. The use of water as a reaction medium is indispensable to ensure high reaction yields.

  带负电的硅铝酸盐层和嵌入其中的路易斯酸性阳离子的使用允许双胺与水溶性醛在水中的有效环缩合。该方案不涉及酸性或回流条件，从而避免了不希望的副产物形成。为了确保高反应产率，使用水作为反应介质是必不可少的。
• Mass Spectrometric Behavior of Thiazide-Based Diuretics after Electrospray Ionization and Collision-Induced Dissociation
  作者：Mario Thevis、Hans Schmickler、Wilhelm Schänzer

  DOI：10.1021/ac020020e

  日期：2002.8.1

  The mass spectrometric behavior of 21 thiazide-based compounds after electrospray ionization in the negative ion mode and collision-induced dissociation was investigated on a triple-stage quadrupole mass spectrometer. The mass spectra show individual and common fragmentation patterns, the generations of which are discussed based on comparable molecular structures of commercially available substances and the synthesis of unlabeled, deuterated, and 15N-labeled analogues. The synthesis of deuterated thiazides is perfomed by condensation of 4-amino-6-chloro-1,3-benzenedisulfonamide with appropriately labeled aldehydes, while the introduction of 15N into the sulfonamide groups of thiazides was achieved by the synthesis of 4-amino-6-chloro-1,3-benzenedisulfonamide(15N2) from 3-chloroaniline via 4-amino-6-chloro-1,3-benzenedisulfonyl chloride. The most common fragments determined are m/z 269, 205, and 126 for 6-chloro-7-sulfamoyl-3-alkyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides and m/z 303, 239, and 160 for 6-trifluoromethyl-7-sulfamoyl-3-alkyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides. Individual fragmentation behaviors were found that mainly depended on the C-3-linked side chain.

  在三级四极杆质谱仪上研究了 21 种噻嗪类化合物在负离子模式下电喷雾电离和碰撞诱导解离后的质谱行为。根据市售物质的可比分子结构以及未标记、氚标记和 15N 标记类似物的合成情况，讨论了这些物质的生成过程。氘代噻嗪类药物的合成是通过 4-氨基-6-氯-1,3-苯二磺酰胺与适当标记的醛缩合实现的，而将 15N 引入噻嗪类药物的磺酰胺基团则是通过 4-氨基-6-氯-1,3-苯二磺酰氯从 3-氯苯胺合成 4-氨基-6-氯-1,3-苯二磺酰胺（15N2）实现的。测定的最常见碎片为：6-氯-7-磺酰胺基-3-烷基-3,4-二氢-1,2,4-苯并噻二嗪-1,1-二氧化物的 m/z-269、205 和 126，以及 6-三氟甲基-7-磺酰胺基-3-烷基-3,4-二氢-1,2,4-苯并噻二嗪-1,1-二氧化物的 m/z-303、239 和 160。所发现的单个碎裂行为主要取决于与 C-3 链接的侧链。
• Palladium-Catalyzed Aminosulfonylation of <i>ortho</i>-Iodoanilines with the Insertion of Sulfur Dioxide for the Synthesis of 3,4-Dihydro-benzothiadiazine 1,1-Dioxides
  作者：Zhenjie Qi、Simiaomiao Wen、Hao Li、Shuai Liu、Dongfang Jiang

  DOI：10.1021/acs.orglett.3c02683

  日期：2023.10.13

  4-dihydro-benzothiadiazine 1,1-dioxides, which are formed through aminosulfonylation of ortho-iodoanilines with SO2. DABSO is utilized as the source of SO2, and the organic compound O2 acts as an oxidant. This direct C–S, S–N, and C–N functionalization is highly efficient, and broad functional group tolerance is observed, resulting in moderate to excellent yields of 3,4-dihydro-benzothiadiazine 1,1-dioxides. Furthermore

  开发了一种简单高效的 Pd 催化氧化环化系统，用于化学和区域选择性合成 3,4-二氢苯并噻二嗪 1,1-二氧化物，该化合物是通过邻碘苯胺与 SO 2 的氨基磺酰化形成的。DABSO用作SO 2源，有机化合物O 2用作氧化剂。这种直接的 C-S、S-N 和 C-N 官能化非常有效，并且观察到广泛的官能团耐受性，从而产生中等至优异的 3,4-二氢-苯并噻二嗪 1,1-二氧化物。此外，该方法适合克级合成。
• Synthesis of Potential Diuretic Agents. I. Derivatives of 7-Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-Dioxide
  作者：W. J. Close、Leo R. Swett、Leonard E. Brady、James H. Short、Maynette Vernsten

  DOI：10.1021/ja01490a028

  日期：1960.3