2,2-二氯-N-(2,6-二甲基苯基)乙酰胺 | 39084-88-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2-二氯-N-(2,6-二甲基苯基)乙酰胺
• 中文别名: 丙胺卡因杂质A
• 英文名称: 2,2-dichloro-N-(2,6-dimethylphenyl)acetamide
• CAS: 39084-88-3
• 化学式: C₁₀H₁₁Cl₂NO
• 分子量: 232.109
• InChiKey: ZBRUDTTYIRXMSM-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C(Solv: ethanol (64-17-5))
• 沸点：
  325.3±42.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090
• 储存条件：
  2-8°C

制备方法与用途

N-(2,6-二甲基苯基)-2,2-二氯乙酰胺用作制备雷诺拉嗪的中间体，而雷诺拉嗪则是一种用于治疗心绞痛的药物。

反应信息

• 作为产物：
  描述：

  N-(2,6-二甲基苯基)-3-氧代丁酰胺 在 N-氯代丁二酰亚胺 、 C₂₀H₂₇N₃O₂S 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到2,2-二氯-N-(2,6-二甲基苯基)乙酰胺
  参考文献：
  名称：

  Zwitterion-Catalyzed Deacylative Dihalogenation of β-Oxo Amides

  摘要：

  alpha,alpha-Dihalo-N-arylacetamides are commonly used as intermediates in various organic reactions. In the study described here, a catalytic synthesis of alpha,alpha-dihalo-N-arylacetamides from beta-oxo amides was developed using zwitterionic catalysts and N-halosuccinimides as the halogen sources. The corresponding alpha,alpha-dihalo-N-arylacetamides were obtained in good to excellent yields, and no aromatic halogenated side products were detected. The reaction conditions were mild, and no strong base or acid was required.

  DOI：

  10.1021/acs.orglett.0c02701

文献信息

• Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent
  作者：David M. Heard、Alastair J. J. Lennox

  DOI：10.1021/acs.orglett.1c00850

  日期：2021.5.7

  dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

  引入二氯甲mel酸是一种稳定的，不挥发的试剂，用于苯胺和烷基胺的二氯乙酰化，以生产α，α-二氯乙酰胺，这是药物化学的重要主题。使用试剂级溶剂可形成高至极佳收率的产物，并且由于唯一的副产物是丙酮和CO 2，因此无需柱色谱法。因此，该试剂对于伯胺的二氯乙酰化是实用，有效和绿色的。
• PREPARATION OF RANOLAZINE
  申请人：Anumula Raghupathi Reddy

  公开号：US20110151258A1

  公开（公告）日：2011-06-23

  Preparation of ranolazine and intermediates thereof, for use in pharmaceutical compositions comprising ranolazine.

  制备拉诺拉嗪及其中间体，用于制备包含拉诺拉嗪的药物组合物。
• Improved Process for Ranolazine: An Antianginal Agent
  作者：Sampath Aalla、Goverdhan Gilla、Raghupathi Reddy Anumula、Srinivas Kurella、Pratap Reddy Padi、Prabhakar Reddy Vummenthala

  DOI：10.1021/op300026r

  日期：2012.5.18

  An improved process has been developed for the active pharmaceutical ingredient, ranolazine with 99.9% purity and 47% overall yield (including three chemical reactions and one recrystallization). Formation and control of all the possible impurities is described. All the solvents used in the process were recovered and reused. The unreacted piperazine is recovered as piperazine monophosphate monohydrate salt.
• Kumar, B.H. Arun; Gowda, B. Thimme, Journal of the Indian Chemical Society, 2002, vol. 79, # 3, p. 231 - 235
  作者：Kumar, B.H. Arun、Gowda, B. Thimme

  DOI：——

  日期：——
• [EN] PREPARATION OF RANOLAZINE<br/>[FR] PRÉPARATION DE RANOLAZINE
  申请人：REDDYS LAB LTD DR

  公开号：WO2010025370A2

  公开（公告）日：2010-03-04

  Preparation of ranolazine and intermediates thereof, for use in pharmaceutical compositions comprising ranolazine.