反応 #411899

反応方程式

toluene

4-diphenylaminoaniline

calcium chloride

aluminum chloride

→

title compound

収率 66.9%

bis(4-diphenylaminophenyl)amine

収率 66.9%

溶媒

—

ice water

tridecane

反応条件

後処理

1. 1
   その他The resulting mixture was reacted at 210 to 220° C. for 3 hours under a nitrogen atmosphere
2. 2
   温度After cooling
3. 3
   workup.STIRRINGThe resulting mixture was stirred
4. 4
   その他the resulting water layer was separated out
5. 5
   洗浄The organic layer was washed successively with 90 ml of a 5% aqueous solution of hydrochloric acid, 60 ml of a 5% aqueous solution of sodium bicarbonate and 60 ml of water
6. 6
   その他After removal of the organic solvent
7. 7
   workup.DISTILLATIONby distillation under reduced pressure, 72 ml of isopropyl alcohol
8. 8
   workup.ADDITIONwas added to the residue
9. 9
   その他the mixture was crystallized overnight at −3 to −8C
10. 10
    ろ過The resulting crude crystals were collected by filtration
11. 11
    洗浄washed with 27 ml of isopropyl alcohol
12. 12
    その他dried

実験手順

In a 500-ml four-necked flask were charged 68 ml of tridecane (boiling point: 234° C.) as a solvent and 130.2 g (0.50 mol) of 4-diphenylaminoaniline, followed by the addition of 15.4 g (0.138 mol) of anhydrous calcium chloride and 18.5 g (0.138 mol) of anhydrous aluminum chloride under stirring. The resulting mixture was reacted at 210 to 220° C. for 3 hours under a nitrogen atmosphere. After cooling, the reaction mixture was added with 114 ml of toluene, followed by charging in 144 g of ice water. The resulting mixture was stirred and allowed to stand, and then the resulting water layer was separated out. The organic layer was washed successively with 90 ml of a 5% aqueous solution of hydrochloric acid, 60 ml of a 5% aqueous solution of sodium bicarbonate and 60 ml of water. After removal of the organic solvent by distillation under reduced pressure, 72 ml of isopropyl alcohol was added to the residue and the mixture was crystallized overnight at −3 to −8C. The resulting crude crystals were collected by filtration, washed with 27 ml of isopropyl alcohol and then dried, whereby 84.2 g (yield: 66.9%) of the title compound was obtained as pale yellow crystals. As a result of HPLC. analysis (column: YMC-A-312, detection UV: 280 nm, flow rate: 1.0 ml/min, eluent: methanol/tetrahydrofuran=99/1), the compound was found to have a purity of 99.7%.

出典