3-特戊酰胺苯甲醚(N-(3-甲氧基苯基)新戊酰胺)主要用于医药、农药等领域,具体用途需结合其化学结构和相关研究文献进一步明确。
医药; 农药
合成路线 1(1. 合成:56619-93-3)
产率:99.5%
合成条件:With sodium carbonate monohydrate In water; ethyl acetate at 0℃; for 1 h; Inert atmosphere
实验步骤:N-(3-甲氧基苯基)新戊酰胺(1a)的合成在氩气氛下,将新戊酰氯(25.0mL,205mmol,市售产品)在0℃下缓慢滴加到包含间 - 茴香胺(21.9mL,195)的混合溶液中。 mmol,市售产品),碳酸钠一水合物的乙酸乙酯(EtOAc)(300mL)(62.0g,500mmol,市售产品)和纯化水(860mL)。 将混合物在0℃下搅拌1小时后,分离有机层,水层用乙酸乙酯(EtOAc)萃取。 将合并的有机层用硫酸钠干燥并过滤。 减压浓缩滤液。 将残余物用乙酸乙酯(EtOAc)重结晶,由此得到N-(3-甲氧基苯基)新戊酰胺(化合物1a)(40.2g,194mmol,99.5%),为无色固体。 TLC Rf = 0.50(正己烷/ EtOAc = 6/1)
参考文献:
- [1] Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 1150 - 1160 [2] Patent: EP2881397, 2015, A1. Location in patent: Paragraph 0053; 0054; 0055 [3] Patent: US2016/303089, 2016, A1. Location in patent: Paragraph 0161; 0162; 0163; 0164 [4] Patent: WO2004/103996, 2004, A1. Location in patent: Page 51 [5] Synlett, 2011, # 7, p. 1018 - 1022 [6] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 9, p. 1333 - 1335 [7] Synthesis (Germany), 2017, vol. 49, # 1, p. 181 - 187 [8] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890 [9] Synthesis (Germany), 2014, vol. 46, # 13, p. 1773 - 1778 [10] Journal of Organic Chemistry, 1988, vol. 53, # 12, p. 2844 - 2847 [11] Journal of Organic Chemistry, 2018, vol. 83, # 8, p. 4812 - 4823 [12] European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 2726 - 2732 [13] Journal of Fluorine Chemistry, 2010, vol. 131, # 7, p. 800 - 804 [14] Journal of the American Chemical Society, 2010, vol. 132, # 37, p. 12862 - 12864 [15] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4681 - 4685 [16] Chemical Communications, 2014, vol. 50, # 94, p. 14862 - 14865 [17] Angewandte Chemie - International Edition, 2015, vol. 54, # 49, p. 14866 - 14870 [18] Angew. Chem., 2015, vol. 127, # 49, p. 15079 - 15083,5 [19] Patent: WO2016/34512, 2016, A1. Location in patent: Page/Page column 72 [20] Green Chemistry, 2017, vol. 19, # 9, p. 2111 - 2117 [21] Organic Letters, 2018, vol. 20, # 3, p. 676 - 679 [22] Angewandte Chemie - International Edition, 2018, vol. 57, # 29, p. 9108 - 9112 [23] Angew. Chem., 2018, vol. 130, p. 9246 - 9250,5
合成路线 2(2. 合成:56619-93-3)
产率:91%
合成条件:With potassium carbonate In acetone for 3 h; Heating / reflux
实验步骤:N-(3-甲氧基苯基)新戊酰胺的合成向1000mL圆底烧瓶中加入N-(3-羟基苯基)新戊酰胺(13.4g,69.43mmol,1.00当量)在丙酮(500mL)中的溶液。 向其中加入K 2 CO 3(28.5g,206.52mmol,3.00当量)。 向混合物中加入MeI(39.4g,277.46mmol,4.00当量)。 使所得溶液在搅拌下反应3小时,同时将温度保持在油浴中回流。 通过TLC(EtOAc / PE = 1:2)监测反应进程。 进行过滤。 使用旋转蒸发器在真空下蒸发浓缩滤液。 用己烷洗涤所得混合物。 进行过滤。 这样得到13.9g(91%)N-(3-甲氧基苯基)新戊酰胺,为白色固体。
参考文献:
- [1] Tetrahedron, 1995, vol. 51, # 45, p. 12263 - 12276 [2] Patent: US2008/318941, 2008, A1. Location in patent: Page/Page column 38-39 [3] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 127-128 [4] Patent: US2008/200471, 2008, A1. Location in patent: Page/Page column 60; 61 [5] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 35 [6] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 92 [7] Patent: US2010/29629, 2010, A1. Location in patent: Page/Page column 61 [8] Patent: WO2010/24980, 2010, A1. Location in patent: Page/Page column 110 [9] Patent: US2010/22581, 2010, A1. Location in patent: Page/Page column 45; 46