반응 #532191

반응 방정식

sodium acetate

sodium nitrite

4-chlorothiophenol

sulfuric acid

2-(3-Methylpiperazin-1-yl)phenylamine

→

1-[2-(4-Chlorophenylsulfanyl)phenyl]-3-methylpiperazine

용매

NaOH

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도the reaction mixture was heated to 60° C. for 30 minutes
3. 3
   온도to cool to room temperature
4. 4
   여과The reaction mixture was filtered
5. 5
   기타the layers were separated
6. 6
   추출The aqueous layer was extracted with ethyl acetate (2×10 mL)
7. 7
   건조The combined organic phases were dried (MgSO4) and volatile solvents
8. 8
   기타evaporated in vacuo
9. 9
   기타The crude product was purified by flash chromatography
10. 10
    세척eluting with ethyl acetate/methanol/ammonia 96:3:1
11. 11
    기타The pure product was isolated as a colourless oil
12. 12
    기타Yield (0.18 g, 11%) 1H NMR (CDCl3, 500 MHz) 1.12 (d, 3H); 2.6-2.72 (br m, 2H); 3.0-3.15 (m, 5H); 6.9 (m, 2H); 7.08 (d, 1H); 7.15 (m, 1H); 7.25-7.35 (m, 4H)

실험 절차

2-(3-Methylpiperazin-1-yl)phenylamine (0.96 g, 5 mmol) was dissolved in 30 mL water containing sulfuric acid (0.28 mL, 5.2 mmol) and the solution was cooled to 0° C. and sodium nitrite (0.36 g, 5.2 mmol) was added. The reaction was stirred for 30 minutes before the pH of the reaction was adjusted to pH 7 with sodium acetate. The diazonium salt solution was then added dropwise to a solution of 4-chlorothiophenol in a suspension of copper (0.3 g, 5 mmol) in 2 M NaOH (4 mL). After addition, the reaction mixture was heated to 60° C. for 30 minutes before being allowed to cool to room temperature and ethyl acetate (10 mL) was added. The reaction mixture was filtered and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic phases were dried (MgSO4) and volatile solvents evaporated in vacuo. The crude product was purified by flash chromatography using silica gel, eluting with ethyl acetate/methanol/ammonia 96:3:1. The pure product was isolated as a colourless oil. Yield (0.18 g, 11%) 1H NMR (CDCl3, 500 MHz) 1.12 (d, 3H); 2.6-2.72 (br m, 2H); 3.0-3.15 (m, 5H); 6.9 (m, 2H); 7.08 (d, 1H); 7.15 (m, 1H); 7.25-7.35 (m, 4H); MS (MH+) 319.1.

출처