3,4-双(环丙基甲氧基)-n-(3,5-二氯吡啶-4-基)苯甲酰胺 | 1391052-24-6

• 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: 3,4-双(环丙基甲氧基)-n-(3,5-二氯吡啶-4-基)苯甲酰胺
• 中文别名: N-(3,5-二氯吡啶-4-基)-3,4-双环丙基甲氧基苯甲酰胺
• 英文名称: 3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide
• 英文别名: 3,4-Bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)benzamide；3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)benzamide
• CAS: 1391052-24-6
• 化学式: C₂₀H₂₀Cl₂N₂O₃
• 分子量: 407.296
• InChiKey: YQDXYEVCMGROIA-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±45.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为产物：
  描述：

  3,4-bis(cyclopropylmethoxy)benzaldehyde 在 sodium chlorite 、 氯化亚砜 、 氨基磺酸 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 3,4-双(环丙基甲氧基)-n-(3,5-二氯吡啶-4-基)苯甲酰胺
  参考文献：
  名称：

  Synthesis of An Impurity in Crude Roflumilast

  摘要：

  A simple synthetic method has been developed for the synthesis of 3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide (an impurity in crude roflumilast) from 3,4-dihydroxybenzaldehyde via alkylation, oxidation, chlorination and acylation reactions. Acetonitrile was used as the solvent in all the three steps for convenient recovery. The oxidation of 3,4-bis(cyclopropylmethoxy) benzaldehyde (purity, 86.2%) by sodium chlorite afforded the corresponding acid with purity of 99.2%. Finally, N-acylation of 3,5-dichloropyridin-4-amine yielded 3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide. Without column chromatography, the overall yield of the target compound was about 70%.

  DOI：

  10.3184/174751914x14061300074410

文献信息

• Synthesis of An Impurity in Crude Roflumilast
  作者：Hankang Zhang、Yan Lin、Yan Li、Kai Dong、Ligong Chen、Donghua Wang

  DOI：10.3184/174751914x14061300074410

  日期：2014.8

  A simple synthetic method has been developed for the synthesis of 3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide (an impurity in crude roflumilast) from 3,4-dihydroxybenzaldehyde via alkylation, oxidation, chlorination and acylation reactions. Acetonitrile was used as the solvent in all the three steps for convenient recovery. The oxidation of 3,4-bis(cyclopropylmethoxy) benzaldehyde (purity, 86.2%) by sodium chlorite afforded the corresponding acid with purity of 99.2%. Finally, N-acylation of 3,5-dichloropyridin-4-amine yielded 3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide. Without column chromatography, the overall yield of the target compound was about 70%.