Reaction SMILES: [CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].Cl.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(O[Na])(C)=O>O>[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1)[CH3:2]
Reactant: CCc1ccc(N)cc1
Reactant: CC(=O)OC(C)=O
Agent: CC(=O)O[Na]
Agent: Cl
Solvent: O
Product: CCc1ccc(NC(C)=O)cc1
Temperature: 0 °C
Reaction time: 0.5 h
Yield: 80.7 %

Procedure:
The starting material for the title compound N,N'-di(p-ethylphenyl)-N,N'-di(phenyl)-1,1'-biphenyl-4,4'-diamine was prepared in three steps as follow: In a 1 L flask, water (750 mL), p-ethylaniline (50 g, 0.41 mol) and conc. HCl (36 mL) were added. Acetic anhydride (42 g, 0.41 mol) was then poured into the solution and then an aqueous solution of AcONa--3H2O (109 g in 170 mL of water) was added. After the addition was complete, the mixture was stirred for 30 minutes, and then ice (500 g) was added. Resulting precipitates were separated by filtration and washed with water. The precipitates were dissolved into CH2Cl2 and washed with water. Organic layer was separated and dried over Na2SO4. Solvent was removed and the residue was recrystallized from MeOH to give p-ethylacetanilide (54.0 g, colorless needles, m.p.=94°-96° C.). In a 5 L three-necked round bottomed flask, p-ethylacetanilide (25 g), bromobenzene (31.2 g), potassium carbonate (25.4 g), copper powder (9.0 g) were added and refluxed for 120hours under an atmosphere of nitrogen. After the reaction was completed, the solution of KOH/EtOH (29.0 g of KOH in 130 mL ethanol) was added to the reaction mixture and heated to reflux for 1 hour. After the reaction was completed, the reaction mixture was cooled to about 25° C. and the precipitate was filtered. The filtrate was poured into water and extracted with CH2Cl2. Organic layer was thoroughly washed with water and the solvent was removed under reduced press (183°-187° C./12 mmHg). The residue was distilled under reduced pressure to give N,N-phenyl-p-ethylphenylamine (17.7 grams) as a pale yellow solid (m.p.=90°-93° C.). In a 500 mL-three-necked round bottomed flask, N,N-phenyl-p-wthylphenylamine (16.5 g), 4,4'-diiodobiphenyl (15.4 g, 0.052 mol), potassium carbonate (15.8 g) and copper(II) sulfate pentahydrate(0.1 g) were added and then heated at 250° C. for 3hours under an atmosphere of nitrogen. The reaction mixture was cooled and 50 mL of toluene and 50 mL of n-Hexane were added. The mixture was filtered through activated alumina (150 g), eluted with the mixed solution of toluene/n-hexanes(1/1 by volume). The solvent was removed and the residue was recrystallized from toluene/acetone to afford N,N'-di(p-ethylphenyl)-N,N'-di(p-phenyl)-1,1'-biphenyl-4,4'-diamine as pale yellow powder (11.4 g, m.p. 156.5°-157.5° C.). To a three necked round bottom flask equipped with a condenser, addition funnel and an argon inlet was added N,N'-di(p-ethylphenyl)-N,N'-di(p-phenyl)-1,1'-biphenyl-4,4'-diamine (8.9 g, 16.4 mmol), methylene chloride (35 mL) and DMF (6 mL). To the resulting solution was added POCl3 (4.5 mL) drop wise over about 30 minutes. The resulting mixture was refluxed for about 24 hours. Upon cooling methylene chloride (150 mL) was added and the solution was poured into water (150 mL). Potassium carbonate (35 g) was added and stirred for 1 hour. The organic layer was separated and washed with water (100 mL), followed by drying over sodium sulfate and concentrating in vacuo to give a solid (11.4 g). This was recrystallized from hexanes/methylene chloride to give a light yellow solid (7.8 g, 79.6% yield).