반응 #351209

반응 방정식

p-Anisoyl chloride

N-phenyl-1,2-phenylenediamine

triethylamine

→

title compound

수율 62.2%

4-methoxy-N-(2-phenylaminophenyl)benzamide

수율 62.2%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise over a 20 minute period
2. 2
   온도while maintaining a temperature of <5° C
3. 3
   세척The organic solution was washed successively with water (200 ml), 2N aqueous HCl (80 ml), and saturated brine solution (160 ml)
4. 4
   건조dried over sodium sulfate
5. 5
   세척The silica was eluted with ethyl acetate (1 L)
6. 6
   기타the eluent was evaporated in vacuo to a pink solid
7. 7
   기타The solid was triturated overnight with ethyl ether (350 ml)
8. 8
   온도cooled in an ice bath
9. 9
   여과filtered
10. 10
    기타dried in vacuo

실험 절차

A vigorously stirring solution of N-phenyl-1,2-phenylenediamine (20.15 g) in dichloromethane (325 ml) and triethylamine (11.07 g) was cooled in an ice/acetone bath under nitrogen. p-Anisoyl chloride (18.66 g) dissolved in dichloromethane (100 ml) was added dropwise over a 20 minute period while maintaining a temperature of <5° C. The reaction mixture was allowed to warm to ambient temperature and stirred for two hours. The organic solution was washed successively with water (200 ml), 2N aqueous HCl (80 ml), and saturated brine solution (160 ml), then dried over sodium sulfate and passed through a pad of silica (150 g). The silica was eluted with ethyl acetate (1 L) and the eluent was evaporated in vacuo to a pink solid. The solid was triturated overnight with ethyl ether (350 ml), cooled in an ice bath, filtered, and dried in vacuo to give the title compound as a light pink solid (21.67 g). 1H (300 MHz, CDCl3): d 3.82 (s, 3H), 5.75 (br s, 1H), 6.80-6.91(m, 5H), 7.12-7.29 (m, 5H), 7.62 (d, J=8.8 Hz, 2H), 8.15 (dd, J=1.7, 7.8 Hz, 1H), 8.36 (s, 1H); TLC (EtOAc/Hex, 1:4): Rf =0.24; m.p.: 148°-150° C.

출처