Reaktion #48181

Reaktionsgleichung

4-[(2-bromo-propyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

4-hydroxy-thiophenol

potassium carbonate

ethyl acetate

→

4-{[3-(4-Hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was transferred into a separation funnel
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with brine (30 mL)
4. 4
   Trocknendried over sodium sulphate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography (eluent: ethyl acetate, Rf: 0.31)
7. 7
   Sonstigeto give an yellow oil, which
8. 8
   Sonstigewas crystallised from methanol

Vorschrift

A mixture of 4-[(2-bromo-propyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02180, 146 mg, 0.50 mmol), 4-hydroxy-thiophenol (240 mg, 1.0 mmol) and potassium carbonate (276 mg, 2.0 mmol) in DMF (10 mL) was stirred for 48 hours at room temperature. The mixture was transferred into a separation funnel and ethyl acetate (50 mL) and water (50 mL) were added. The organic layer was separated, washed with brine (30 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate, Rf: 0.31) to give an yellow oil, which was crystallised from methanol. Yield: 211 mg (60%). 1H-NMR (400 MHz, d6-DMSO) δ=1.64 (tt, J=7.0, 7.0 Hz, 2H), 2.89 (t, J=7.0 Hz, 2H), 3.92 (t, J=7.0 Hz, 2H), 6.57 (d, J=9.0 Hz, 2H), 6.72 (d, J=9.0 Hz, 2H), 7.20 (d, J=9.0 Hz, 2H), 7.71 (d, J=9.0 Hz, 2H), 8.96 (s, 2H), 9.59 (s, 1H, —OH). LRMS (FAB+): 352.1 (100, [M+H]+).

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