Reaktion #1798522

Reaktionsgleichung

Compound C4

N-(4-Nitrophenyl)-3-(4-pyridinylamino)benzamide

methyl-p-toluenesulfonate

→

C5

Ausbeute 97.0%

1-Methyl-4-{3-[(4-nitroanilino)carbonyl]anilino}pyridinium 4-methylbenzenesulfonate

Ausbeute 97.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSolvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in warm MeOH (10 mL)
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   workup.WAITthe solution was then refrigerated for 18 h
5. 5
   FiltrationThe resulting precipitate was filtered
6. 6
   Waschenwashed with EtOAc

Vorschrift

Compound C4 (1.92 g, 5.73 mmol) was suspended in DMF (10 mL), methyl-p-toluenesulfonate (15 mL) was added, and the mixture was stirred at room temperature for 18 h. Solvent was removed under reduced pressure and the residue was dissolved in warm MeOH (10 mL), then diluted with EtOAc. Some of the MeOH was boiled off, and the solution was then refrigerated for 18 h. The resulting precipitate was filtered, and washed with EtOAc to give essentially pure C5 (2.90 g, 97%), which was used without further purification. 1H NMR [(CD3)2SO] δ 10.85 (s, 1H, CONH), 10.60 (s, 1H, NH), 8.33-8.27 (m, 4H, H-3′, 5′ & py H-2, 6), 8.08-8.30 (m, 2H, H-2′, 6′), 7.94-7.89 (m, 2H, H-2″4″), 7.69 (t, J=7.9 Hz, 1H, H-5″), 7.60-7.57 (m, 1H, H-6″), 7.48-7.45 (m, 2H, H-3, 5), 7.22 (d, J=7.5 Hz, 2H, p-tol H-2, 6), 7.20 (d, J=8.1 Hz, 2H, p-tol H-3, 5), 3.99 (s, 3H, N+CH3), 1.99 (s, 3H, CH3).

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