ethyl N-[(4-aminophenyl)methylsulfonyl]-N-methylcarbamate | 765252-40-2

• 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: ethyl N-[(4-aminophenyl)methylsulfonyl]-N-methylcarbamate
• CAS: 765252-40-2
• 化学式: C₁₁H₁₆N₂O₄S
• 分子量: 272.325
• InChiKey: HKIVUKDTQZZKSO-UHFFFAOYSA-N

物化性质

• 沸点：
  433.5±47.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 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：
  98.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-[(4-aminophenyl)methylsulfonyl]-N-methylcarbamate 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (Z)-4-{2-[4-(dimethylamino)butylidene]hydrazino}-N-ethoxycarbonyl-N-methylbenzenemethanesulphonamide
  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
• 作为产物：
  描述：

  N-ethoxycarbonyl-N-methyl-4-nitrobenzenemethanesulphonamide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 ethyl N-[(4-aminophenyl)methylsulfonyl]-N-methylcarbamate
  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, 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).