Some common heterocyclic compound, 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, molecular formula is C8H5F3N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 2-Amino-5-cyanobenzotrifluoride
i. 4-Dibenzylamino-3-trifluoromethyl-benzonitrile, 2 To a solution of 2-amino-5-cyanobenzotrifluoride (1.0 g, 5.37 mmol, 1 eq) and benzyl bromide (2.55 mL, 21.5 mmol, 4.0 eq) in dry DMF (10 mL) was added at rt NaH (970 mg, 21.5 mmol, 4 eq) portion-wise under Ar (g). The reaction mixture was stirred at rt overnight, and was then partitioned with H2O (30 mL) and extracted with EtOAc (5*20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1) to yield the product, 2, as a pale yellow solid (1.66 g, 85%). 1H NMR (400 MHz, CDCl3) deltaH: 7.95 (d, J=2.0 Hz, 1H), 7.63 (dd, J=8.5, 1.5 Hz, 2H), 7.28-7.34 (m, 6H), 7.20 (d, J=6.5 Hz, 4H), 7.12 (d, J=8.5 Hz, 1H), 4.23 (s, 4H). MS (ES+) 389.1 (100%, [M+Na]+).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-74-2, its application will become more common.
Reference:
Patent; KARUS THERAPEUTICS LIMITED; Shuttleworth, Stephen Joseph; Silva, Franck Alexandre; US2013/109688; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts