4-Methyl-N-(4-methylphenyl)-N-phenylbenzenamine

White to yellow solid

Under a nitrogen atmosphere, In a 200 mL three-necked flask equipped with a stirrer, bromobenzene 7.71g (49.1 mmol), 9.78 g (49.6 mmol) of di-p-tolylamine, 5.70 g (59.3 mmol) of sodium tert-butoxide, Palladium acetate 110 mg (0.490 mmol), 396 mg (1.96 mmol) of tri-tert-butylphosphine, 110 mL of o-xylene was added, and the mixture was stirred at 120°C. for 20 hours. After completion of the reaction, 150 mL of pure water was added, and the mixture was washed and separated. Further, after washing and separating with 150 mL of pure water, then saturated brine, The obtained organic layer was concentrated under reduced pressure, and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography, white crystals 12.9 g (yield 96percent, purity 99.1percent) was obtained.4-Methyl-N-phenyl-N-p-tolylaniline (G)A general procedure for the synthesis of diarylated amines. To a mixture of 1a (257 mg, 1.50 mmol), CsF (228 mg, 1.50 mmol), Pd(dba)General procedure: In a Schlenk tube with a magnetic bar, base (3.0mmol), PdClUnder a nitrogen atmosphere, In a 200 mL three-necked flask equipped with a stirrer, bromobenzene 7.71g (49.1 mmol), 9.78 g (49.6 mmol) of di-p-tolylamine, 5.70 g (59.3 mmol) of sodium tert-butoxide, Palladium acetate 110 mg (0.490 mmol), 396 mg (1.96 mmol) of tri-tert-butylphosphine, 110 mL of o-xylene was added, and the mixture was stirred at 120C. for 20 hours. After completion of the reaction, 150 mL of pure water was added, and the mixture was washed and separated. Further, after washing and separating with 150 mL of pure water, then saturated brine, The obtained organic layer was concentrated under reduced pressure, and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography, white crystals 12.9 g (yield 96%, purity 99.1%) was obtained.N, N-dimethylformamide (2.74 g, 37.5 mmol) was added dropwise to the mixture of TPA (2.27 g, 18.8 mmol) and phosphorous oxychloride (POCl3) (5.65 g, 22.5 mmol) at 25 °C. The reaction mixture was stirred and heated at 130 °C for 6 h. After cooling down to room temperature, the reaction mixture was poured into 50 mL cold water and extracted with chloroform (3 x 15 mL). The combined organic layer was dried with anhydrous MgSO4, filtered. The purified compound R2-CHO was obtained by recrystallizing from diluted ethanol. Yield: 1.75 g (31.5percent). Melting point: 96.3-97.5 °C. ESI-MS (m/z, [M + H]+)=302.4.A suspended solution of Under ice cooling, 1.04 g of tetramethylene sulfoxide was added dropwise to a mixture of 4.10 g of 4, 4?-dimethyltriphenylamine, 8.20 g of Eaton reagent and 8.20 g of dichloromethane. The contents were stirred under ice cooling for 1 hour and at room temperature for a further 16 hours for aging. The reaction mixture was quenched by adding 50 g of water, combined with 30 g of diisopropyl ether, and stirred, after which the water layer was taken out. The water layer was washed 2 times with 30 g of diisopropyl ether, combined with 6.30 g of Sulfonate 1 and 50 g of MIBK, and stirred, after which the organic layer was taken out. The organic layer was washed 7 times with 40 g of water, from which dichloromethane was removed by vacuum concentration. To the concentrate, 50 g of diisopropyl ether was added for crystallization. The resulting solid was dried under reduced pressure, obtaining 5.00 g of the desired compound PAG-4 in solid form (yield 65%). Spectral data of PAG-4 are shown below. IR (D-ATR): nu=3029, 2909, 2854, 1749, 1581, 1508, 1494, 1453, 1376, 1331, 1303, 1279, 1254, 1217, 1195, 1182, 1163, 1082, 1051, 990, 918, 865, 820, 800, 730, 712, 676, 641, 615, 602, 575, 565 cm-1 )1H-NMR (500 MHz, DMSO-d6): delta=1.60-1.70 (6H, m), 1.83 (6H, d), 1.96 (3H, s), 2.22 (2H, m), 2.30 (6H, s), 2.34 (2H, m), 3.56 (2H, m), 3.87 (2H, m), 5.93 (1H, m), 6.83 (2H, m), 7.07 (4H, m), 7.22 (4H, d), 7.64 (2H, m) ppm )191F-NMR (500 MHz, DMSO-d6): delta=-119.5 (1F, m), -113.6 (1F, m), -72.5 (3F, m) ppm )0233) TOF-MS (MALDI): POSITIVE M 360 (corresponding to C24H26NS+) NEGATIVE M- 391 (corresponding to C14H16F5O5S-)

Molecular Weight:273.4
XLogP3:6.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:273.151749610
Monoisotopic Mass:273.151749610
Topological Polar Surface Area:3.2
Heavy Atom Count:21
Complexity:269
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes