4-chloro-N-(cyanomethyl)benzamide | 22198-19-2

• 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: 4-chloro-N-(cyanomethyl)benzamide
• 英文别名: 4-chlorobenzoylaminoacetonitrile
• CAS: 22198-19-2
• 化学式: C₉H₇ClN₂O
• mdl: MFCD01212075
• 分子量: 194.62
• InChiKey: PUWBYORMPOABDI-UHFFFAOYSA-N

物化性质

• 沸点：
  406.3±30.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(cyanomethyl)benzamide 生成 N-(2-amino-1-bromo-2-oxoethyl)-4-chlorobenzamide
  参考文献：
  名称：

  CROWLEY, PATRICK JELF;SHEPHARD, MARGARET CLAIRE

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲酰氯 、 氨基乙腈 在 sodium hydroxide 作用下， 生成 4-chloro-N-(cyanomethyl)benzamide
  参考文献：
  名称：

  Syntheses of 2-Acylaminoacetamidine and 3-Acylaminopropionamidine Derivatives

  摘要：

  为了检测它们的抗病毒活性，通过相应的腈类经由乙基咪唑合成2-酰氨基乙脒（II）和3-酰氨基丙脒盐酸盐（III）。假设了乙基2-酰氨基乙咪唑和乙基3-酰氨基丙咪唑在酰胺化过程中的反应活性差异。通过参考相应的单氰单酯（ethyl p-(N-cyanoethylcarbamoyl) benzoate）（XXI）的红外光谱，讨论了二氰（对-氰基）苯甲酰胺丙腈（XVIII）的亚胺酯化。其中，3-（对-甲基）苯甲酰胺丙脒盐酸盐被发现对小鼠和膜培养中的流感病毒具有抑制作用。

  DOI：

  10.1248/cpb.16.2355

文献信息

• Nickel‐Catalyzed Construction of 2,4‐Disubstituted Imidazoles <i>via</i> C–C Coupling and C−N Condensation Cascade Reactions
  作者：Shengyang Fang、Haihua Yu、Xicheng Yang、Jianqi Li、Liming Shao

  DOI：10.1002/adsc.201900096

  日期：2019.7.11

  A convenient Ni(II)‐catalyzed C−C and C−N cascade coupling reaction was developed to directly access various 2,4‐disubstituted imidazoles. The reaction scope covers a variety of aryl and aliphatic substitutions, which demonstrate moderate‐to‐excellent yields. The tolerance of halogen and N‐containing heterocyclic groups demonstrates the versatility of this method for further synthetic explorations

  开发了一种方便的Ni（II）催化的C-C和C-N级联偶联反应，可直接使用各种2,4-二取代的咪唑。反应范围涵盖了各种芳基和脂肪族取代基，显示出中等至优异的收率。卤素和公差Ñ含杂环基团的演示此方法作进一步的合成探索的多功能性。
• Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
  作者：Ling Dai、Shuling Yu、Ningning Lv、Xuanzeng Ye、Yinlin Shao、Zhongyan Chen、Jiuxi Chen

  DOI：10.1021/acs.orglett.1c01762

  日期：2021.8.6

  efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical

  我们在此报告了一种以单步方式组装多取代咪唑和恶唑的有效方法。这些转化基于容易获得的芳香族羧酸和脂肪族腈的脱羧加成和环化，并表现出良好的官能团兼容性和高步骤经济性。该反应是可扩展的，制备的产品可以转化为实用的骨架。重要的是，莫罗替尼的后期衍生化突出了这种方法的潜在效用。
• Modified method of synthesis of N-substituted dithioesters of amino acids and peptides in the Pinner reaction
  作者：Witold Neugebauer、Eric Pinet、Munsok Kim、Paul R. Carey

  DOI：10.1139/v96-038

  日期：1996.3.1

  An improved method for the synthesis of dithioesters of amino acids and peptides has been developed. The syntheses have been carried out from the nitriles. The addition of thiol to the nitrile derivative in the Pinner step of dithioester synthesis was activated with hydrogen fluoride. A few examples of dithioester synthesis using liquid HF are described. Some novel dithioesters, which are model compounds for resonance Raman spectroscopic studies of dithioacylpapain intermediates, are described. Key words: dithioesters, amino acids, Pinner reaction, HF, isotopes.

  已开发出一种改进的合成氨基酸和肽二硫酯的方法。该合成是从腈中进行的。在二硫酯合成的Pinner步骤中，将硫醇加入到腈衍生物中，使用氢氟酸进行活化。描述了使用液体氢氟酸进行二硫酯合成的几个示例。描述了一些新型二硫酯，这些是用于共振拉曼光谱研究二硫酰基木瓜蛋白酶中间体的模型化合物。关键词：二硫酯，氨基酸，Pinner反应，HF，同位素。
• Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide
  作者：Shaoqing Du、Jin Li、Wen Fu、Xiaoyong Xu、Xusheng Shao、Xuhong Qian

  DOI：10.1016/j.tetlet.2021.153209

  日期：2021.7

  1,2,4-Oxadiazole-3-carboxamide has been extensively used in the pharmaceutical chemistry. In this study, 1,2,4-oxadiazole-3-carboxamide is accomplished through an acid-promoted reaction of N-(cyanomethyl)amide with nitrosation reagent. This novel preparation of 1,2,4-oxadiazole-3-carboxamide was carried out at 25 °C, and the yield of target compounds was as high as 92%. At the same time, the amount

  1,2,4-Oxadiazole-3-carboxamide 已广泛用于药物化学。在这项研究中，1,2,4-oxadiazole-3-carboxamide 是通过N-（氰甲基）酰胺与亚硝化试剂的酸促进反应来完成的。这种1,2,4-恶二唑-3-甲酰胺的新制备在25℃下进行，目标化合物的产率高达92%。同时，减少了酸的用量。已经提供了形成 1,2,4-oxadiazole-3-carboxamide 的机制推测。新的合成方法为含1,2,4-恶二唑-3-甲酰胺化合物的合成提供了极大的便利。
• Preparation of substituted benzamides
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0135304A2

  公开（公告）日：1985-03-27

  Benzamides of the formula (I): in which Ar is optionally substituted aryl; X is 0, S or NH and R is optionally substituted alkyl or alkenyl when X is 0 or S, or is optionally substituted alkenoyl when X is NH, are prepared by (a) reacting a compound of the formula (II): with a brominating agent in a solvent which is substantially chemically inert to the reactants and in which compound (II) is soluble, to form a compound of the formula (III): and (b) reacting the compound (III) with a compound RXH. Preferably, bromination is carried out rapidly in dried ethyl acetate. The process avoids hydration of the CN group of the compound (III) to a carbamoyl group obviating a subsequent dehydration step later. The intermediate compound (III) is novel. The substituted benzamides are useful as herbicides and fungicides.

  式(I)的苯甲酰胺： 其中 Ar 是任选取代的芳基；X 是 0、S 或 NH；当 X 是 0 或 S 时，R 是任选取代的烷基或烯基，或当 X 是 NH 时，R 是任选取代的烯酰基。 (a) 将式 (II) 的化合物 与溴化剂在对反应物基本化学惰性且化合物 (II) 可溶解的溶剂中反应，生成式 (III) 的化合物： 和 (b) 使化合物 (III) 与化合物 RXH 反应。溴化反应最好在干燥的乙酸乙酯中快速进行。 该工艺避免了化合物（III）的 CN 基团水合成为氨基甲酰基，从而省去了随后的脱水步骤。 中间体化合物 (III) 是一种新型化合物。 取代的苯甲酰胺可用作除草剂和杀真菌剂。