3-CYANO-5-NITROBENZOTRIFLUORIDE

To a mixture of 3-nitro-5-(trifluoromethyl)benzamide (1.5 g, 6.41 mmol) in DCM (20mL) were added EtTo a mixture of 3 -nitro-5 -(trifluoromethyl)benzonitrile (400 mg, 1.851 mmol) in DMF (20mL) was added sodium azide (361 mg, 5.55 mmol) at rt. The mixture was stirred at 120 C overnight. LCMS showed the reaction was finished. The reaction was quenched by water. The mixture was extracted with EA (20 mL x 3), washed with water, and concentrated to give 5-(3-nitro-5- (trifluoromethyl)phenyl)-2H-tetrazole (220 mg, 0.743 mmol, 40.1% yield): NMR (400 MHz, DMSO-d6) delta 9.03 (s, 1H), 8.73 (s, 1H), 8.66 (s, 1H), 7.92 (s, 1H). ES-LCMS m/z 260 (M+H).To a mixture of 3-nitro-5-(trifluoromethyl)benzamide (1.5 g, 6.41 mmol) in DCM (20mL) were added Et3N (1.314 mL, 9.61 mmol) and trifluoroacetic anhydride (1.357 mL, 9.61 mmol) at 20 C. The mixture was stirred at 20 C for 2 h. TLC (PE/EA = 3: 1, Rf = 0.6) showed the reaction was finished. The reaction was concentrated to give crude product, which was purified by column chromatography (PE/EA = 3: 1, Rf = 0.6) to give In a Parr shaker flask, compound 35-1 (1 g, 4.63 mmol) was dissolved in EtOH and concentrated HCI (2 mL) was added. The reaction mixture was flushed with nitrogen, Pd/C (0.5 g) was added and the reaction was placed on the Parr shaker at 45 psi hydrogen pressure overnight. The solids were removed by filtration and the solids stripped in vacuo. The product was then taken up in MeOH (10 mL) and diethyl ether was added (100 mL). The product (35-2) was then isolated by filtration.

Molecular Weight:216.12
XLogP3:2.4
Hydrogen Bond Acceptor Count:6
Exact Mass:216.01466183
Monoisotopic Mass:216.01466183
Topological Polar Surface Area:69.6
Heavy Atom Count:15
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes