* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: A 10 mL Schlenk tube was charged with III (0.0128 g, 0.0075 mmol), N,N'-diisopropylcarbodiimide (0.189 g, 1.5 mmol), and aniline (0.140 g, 1.5 mmol) under dried argon. The resulting mixture was stirred at 25 °C for 30 min. The reaction mixture was extracted with ether and filtered to give a clean solution. After removing the solvent under vacuum, the residue was recrystallized in ether to provide a white solid 1 in >99percent yield.
96%
With zinc(II) oxide In toluene at 110℃; for 10 h;
General procedure: A mixture of amine (1 mmol), carbodiimide (1.1 mmol) and nanocrystalline ZnO (20 mol percent, 0.016 g) was stirred in toluene (1 mL) at 80 °C for 8 h (for aromatic and aliphatic primary amines) or at 110 °C for 10 h (for secondary amines). The progress of the reaction was monitored by TLC analysis. At the end of the reaction, the reaction mixture was allowed to cool to room temperature, centrifuged and filtered the supernatant through a sintered funnel. The catalyst was then washed with ethyl acetate, centrifuged and filtered. The combined filtrate was concentrated under reduced pressure, and further purified by column chromatography on neutral alumina using ethyl acetate/hexane as the eluent to afford the desired product in good yields.
96%
With iron(II) acetate In toluene at 140℃; for 5 h; Inert atmosphere
General procedure: A Schlenk tube under nitrogen was charged with Fe(OAc)2 (8.70 mg, 0.05 mmol), the corresponding amine (1 mmol) and carbodiimide (1.2 mmol) and toluene (2 mL). The resulting suspension was heated at 140 oC and the progress of the reaction was monitored by TLC. At the end of the reaction, the reaction mixture was allowed to cool to room temperature and then hydrolyzed with water (5 mL), extracted with dichloromethane (3 10 mL), dried over anhydrous Na2SO4 and filtered. Then, the solvent was evaporated under reduced pressure to give the crude product which was purified by recrystallization method in hexane or diethyl ether and also by column chromatography to afford the desired products in good yields.
96%
With 1,3-di-tert-butylimidazol-2-ylidene:Mg[N(SiMe3)2]2 In toluene at 110℃; for 24 h; Schlenk technique; Inert atmosphere; Glovebox
General procedure: A 30 mL Schlenk tube under inert atmosphere (N2-glovebox) was charged with the catalyst ItBu:Mg[N(SiMe3)2]2 (0.03 equiv), secondary amine (1.0 equiv), and toluene (5 mL). To this mixture carbodiimides (1.0 equiv) was added. The flask was then closed to prevent evaporation of amines with low boiling points, and the resulting mixture was heated to 110 °C for the desired time. The solvent was removed under reduced pressure; the residue was extracted with hexane (3 x 15 mL) and filtered to give a clean solution. After removing the hexane under reduced pressure, the final products were obtained.
Reference：
[1] Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 8966 - 8972
[2] Tetrahedron, 2011, vol. 67, # 45, p. 8790 - 8799
[3] Tetrahedron, 2012, vol. 68, # 29, p. 5730 - 5737
[4] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5156 - 5158
[5] Journal of Organometallic Chemistry, 2014, vol. 769, p. 112 - 118
[6] Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 6347 - 6349
[7] Journal of Organometallic Chemistry, 2012, vol. 713, p. 27 - 34
[8] Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 8, p. 1211 - 1220
2
[ 108-91-8 ]
[ 4975-73-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 22, p. 3693 - 3700
3
[ 36903-85-2 ]
[ 4975-73-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 22, p. 3693 - 3700
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