反応 #715754

反応方程式

biphenyl-3,3′,4,4′-tetraamine

4-aminobenzoic acid

water

→

product

収率 97.5%

4,4′-(1H,3′H-5,5′-Bibenzo[d]imidazole-2,2′-diyl)dianiline

収率 97.5%

溶媒

MeOH

反応条件

後処理

1. 1
   workup.ADDITIONwas added portionwise
2. 2
   workup.STIRRINGThe mixture was stirred at 200° C. for 2.5 h
3. 3
   温度The mixture was cooled (to <100° C.)
4. 4
   workup.STIRRINGThe resulting mixture was stirred until a uniform green precipitate
5. 5
   その他had formed
6. 6
   ろ過The solid was filtered off
7. 7
   洗浄washed with aqueous K2CO3 and water
8. 8
   その他dried under suction
9. 9
   その他The crude product was purified by column chromatography (99:1 EtOAc-NEt3 to 89:10:1 EtOAc-MeOH-NEt3)
10. 10
    その他to afford a yellow solid
11. 11
    濃縮1M HCl, and then concentrated in vacuo
12. 12
    workup.STIRRINGstirred in aqueous NaHCO3
13. 13
    ろ過The solid was filtered
14. 14
    洗浄washed with water
15. 15
    その他dried (vacuum oven)

実験手順

A homogenous mixture of biphenyl-3,3′,4,4′-tetraamine (500 mg, 2.34 mmol) and 4-aminobenzoic acid (640 mg, 4.67 mmol) was added portionwise to stirred PPA (20 mL) at 200° C. The mixture was stirred at 200° C. for 2.5 h. The mixture was cooled (to <100° C.) and poured into water. The resulting mixture was stirred until a uniform green precipitate had formed. The solid was filtered off and washed with aqueous K2CO3 and water, then dried under suction. The crude product was purified by column chromatography (99:1 EtOAc-NEt3 to 89:10:1 EtOAc-MeOH-NEt3) to afford a yellow solid. This was dissolved in MeOH and 1M HCl, and then concentrated in vacuo. The material was then ground to a fine powder and stirred in aqueous NaHCO3. The solid was filtered, washed with water and dried (vacuum oven) to give the product as a yellow solid (475 mg, 49%).

出典