반응 #351214

반응 방정식

Potassium carbonate

N-phenylphenylene diamine

2-bromo-N-isopropyl-N-phenyl acetamide

→

title compound

수율 56.1%

N-isopropyl-N-phenyl-2-(2-phenylaminophenylamino)-acetamide

수율 56.1%

용매

DMF

DMF

반응 조건

후처리

1. 1
   기타The DMF was evaporated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (400 ml)
3. 3
   세척washed exhaustively with aqueous 1N HCl (4×250 ml)
4. 4
   세척The organic layer was washed with water (2×200 ml)
5. 5
   건조dried (Na2SO4)
6. 6
   기타evaporated
7. 7
   기타to give 17.8 gm of crude alkylated product
8. 8
   기타The oil was purified by chromatography on silica gel (600 g)

실험 절차

Potassium carbonate (6.9 g) was added to a solution of N-phenylphenylene diamine (9.2 g) in DMF and 2-bromo-N-isopropyl-N-phenyl acetamide (12.7 g) in DMF (200 ml) and the mixture was allowed to stir overnight. The DMF was evaporated in vacuo and the residue was dissolved in ethyl acetate (400 ml) and washed exhaustively with aqueous 1N HCl (4×250 ml). The organic layer was washed with water (2×200 ml), dried (Na2SO4) and evaporated to give 17.8 gm of crude alkylated product. The oil was purified by chromatography on silica gel (600 g) using first CHCl3 (8000 mL), then hexane:ethyl acetate (2:1, 8000 ml) as eluents to give the title compound (10 g), as an oil. 1H-NMR (300 MHz, CDCl3): d 7.42-6.8 (m, 14 H), 6.36 (d, 1H), 4.95 (m, 1H), 3.22 (s, 2H), 1.05 (d, 6H); MS (FAB)=360 (MH+); TLC, Rf=0.18 (CHCl3).

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