N-ethoxycarbonyl-N-methyl-4-nitrobenzenemethanesulphonamide | 197580-86-2

• 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: N-ethoxycarbonyl-N-methyl-4-nitrobenzenemethanesulphonamide
• 英文别名: ethyl N-methyl-N-[(4-nitrophenyl)methylsulfonyl]carbamate
• CAS: 197580-86-2
• 化学式: C₁₁H₁₄N₂O₆S
• 分子量: 302.308
• InChiKey: RUXFJTMMDPDEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-ethoxycarbonyl-N-methyl-4-nitrobenzenemethanesulphonamide 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium nitrite 作用下， 反应 0.25h， 生成 4-[[Ethoxycarbonyl(methyl)sulfamoyl]methyl]benzenediazonium;chloride
  参考文献：
  名称：

  5-取代吲哚衍生物的合成，第二部分。Japp-Klingemann 反应合成舒马曲坦

  摘要：

  Synthesis of selective 5-HT1B/1D receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the beta-carboline (16).

  DOI：

  10.3987/com-99-8815
• 作为产物：
  描述：

  N-甲基-4-硝基-α-甲苯磺酰胺 、 氯甲酸乙酯 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以96%的产率得到N-ethoxycarbonyl-N-methyl-4-nitrobenzenemethanesulphonamide
  参考文献：
  名称：

  Synthesis of 5-Substituted Indole Derivatives, I. An Improved Method for the Synthesis of Sumatriptan

  摘要：

  An improved synthesis of sumatriptan (Ib) via Fischer cyclization was achieved by introducing the ethoxycarbonyl group on the N-atom of the sulphonamide moiety in N-methyl-4-hydrazinobenzenemethanesulphonamide (7). As a result, substitution on the benzylic carbon of the indole nucleus could be avoided; however, formation of 1,1-bis-(indol-2-yl)-4-dimethylaminobutane-type by-product (19) was observed. The indolization procedure was optimized to suppress the unwanted side reaction. The N-protection of the sulphonamide moiety was found to be beneficial regarding the purification of the 3-[2-(dimethylamino)ethyl]-N-ethoxycarbonyl-N-methyl-1H-indole-5-methanesulphonamide (18).

  DOI：

  10.3987/com-97-8087

文献信息

• Synthesis of 5-Substituted Indole Derivatives, Part II. Synthesis of Sumatriptan through the Japp-Klingemann Reaction
  作者：Béla Pete、István Bitter、Kálmán Harsányi、László Tõke

  DOI：10.3987/com-99-8815

  日期：——

  Synthesis of selective 5-HT1B/1D receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the beta-carboline (16).
• Synthesis of 5-Substituted Indole Derivatives, I. An Improved Method for the Synthesis of Sumatriptan
  作者：Béla Pete、István Bitter、Csaba Szántay, Jr.、István Schön、László Töke

  DOI：10.3987/com-97-8087

  日期：——

  An improved synthesis of sumatriptan (Ib) via Fischer cyclization was achieved by introducing the ethoxycarbonyl group on the N-atom of the sulphonamide moiety in N-methyl-4-hydrazinobenzenemethanesulphonamide (7). As a result, substitution on the benzylic carbon of the indole nucleus could be avoided; however, formation of 1,1-bis-(indol-2-yl)-4-dimethylaminobutane-type by-product (19) was observed. The indolization procedure was optimized to suppress the unwanted side reaction. The N-protection of the sulphonamide moiety was found to be beneficial regarding the purification of the 3-[2-(dimethylamino)ethyl]-N-ethoxycarbonyl-N-methyl-1H-indole-5-methanesulphonamide (18).