N-(4,5-dimethyl-thiazol-2-yl)-N-methylaniline | 1130966-01-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4,5-dimethyl-thiazol-2-yl)-N-methylaniline
• 英文别名: N,4,5-trimethyl-N-phenylthiazol-2-amine；N,4,5-trimethyl-N-phenyl-1,3-thiazol-2-amine
• CAS: 1130966-01-6
• 化学式: C₁₂H₁₄N₂S
• 分子量: 218.323
• InChiKey: IGQRFUIYUIQRBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5-二甲基噻唑 、 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 20.0h， 以73%的产率得到N-(4,5-dimethyl-thiazol-2-yl)-N-methylaniline
  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.
• Cu(acac)2 catalyzed oxidative C–H bond amination of azoles with amines under base-free conditions
  作者：Yogesh S. Wagh、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2012.09.064

  日期：2012.11

  This work reports a simple and efficient methodology for oxidative C-H bond amination of azoles with aromatic/aliphatic amines using copper-bis-acetylacetonate complex catalyst. The catalyst works very well in the absence of external acid or base and requires only molecular oxygen as an oxidant. The methodology is applicable for the oxidative C-H bond amination of various azoles with different types of aromatic/aliphatic amines for the synthesis of various aminoheterocycles with good to excellent yields. (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.