2-(N-methyl-N-phenylamino)-5-(4-ethoxycarbonylphenyl)thiazole | 1130966-19-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(N-methyl-N-phenylamino)-5-(4-ethoxycarbonylphenyl)thiazole
• 英文别名: ethyl 4-[2-(methyl(phenyl)amino)-thiazol-5-yl]benzoate；ethyl 4-[2-(N-methylanilino)-1,3-thiazol-5-yl]benzoate
• CAS: 1130966-19-6
• 化学式: C₁₉H₁₈N₂O₂S
• 分子量: 338.43
• InChiKey: IHQQSAMVIXCNQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  70.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl p-(5-thiazolyl)benzoate 、 N-甲基苯胺 在 氧气 、 copper diacetate 、 sodium acetate 、 三苯基膦 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以68%的产率得到2-(N-methyl-N-phenylamino)-5-(4-ethoxycarbonylphenyl)thiazole
  参考文献：
  名称：

  Direct Amination of Azoles via Catalytic C−H, N−H Coupling

  摘要：

  C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.

  DOI：

  10.1021/ol900298e

文献信息

• Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes
  作者：Shinobu Mitsuda、Taiki Fujiwara、Katsuyoshi Kimigafukuro、Daiki Monguchi、Atsunori Mori

  DOI：10.1016/j.tet.2012.03.001

  日期：2012.5

  C-H, N-H coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)(2) and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)(2)-2PPh(3) and 4 equiv of NaOAc under O-2 or in the presence of Ag2CO3 under N-2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended pi-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag2CO3 as an additive and Cu(OAc)2-2PPh3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo C-H, N-H amidation. (C) 2012 Elsevier Ltd. All rights reserved.
• Direct Amination of Azoles via Catalytic C−H, N−H Coupling
  作者：Daiki Monguchi、Taiki Fujiwara、Hirotoshi Furukawa、Atsunori Mori

  DOI：10.1021/ol900298e

  日期：2009.4.2

  C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.