Reaktion #48186

Reaktionsgleichung

4-[(2-Bromo-pentyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

4-hydroxy-thiophenol

potassium carbonate

ethyl acetate

→

4-{[5-(4-Hydroxy-phenylsulfanyl)-pentyl]-[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: 0.43)
7. 7
   workup.DISSOLUTIONThe resulting yellow oil was dissolved in ethyl acetate
8. 8
   Sonstigeprecipitated by addition of hexane
9. 9
   Sonstigeto give an light yellow powder

Vorschrift

A mixture of 4-[(2-Bromo-pentyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB03005, 500 mg, 1.5 mmol), 4-hydroxy-thiophenol (378 mg, 3.0 mmol) and potassium carbonate (414 mg, 3.0 mmol) in DMF (10 mL) was stirred for 12 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: 0.43). The resulting yellow oil was dissolved in ethyl acetate and precipitated by addition of hexane to give an light yellow powder. Yield: 338 mg (59%). 1H-NMR (400 MHz, d6-DMSO) δ=1.40-1.54 (m, 6H), 2.77 (t, J=6.8 Hz, 2H), 3.79 (t, J=6.6 Hz, 2H), 6.61 (d, J=9.0 Hz, 2H), 6.72 (d, J=9.0 Hz, 2H), 7.20 (d, J=9.0 Hz, 2H), 7.72 (d, J=9.0 Hz, 2H), 8.96 (s, 2H), 9.55 (s, 1H. —OH). 13C-NMR (100 MHz, d6-DMSO) δ=25.66, 26.67, 29.35, 35.56, 53.86, 103.06, 113.89, 116.80, 119.84, 124.54, 133.39, 134.47, 144.09, 151.89, 157.26. LRMS (FAB+): 380.0 (100, [M+H]+). LRMS (FAB+) 380.15355 C20H22N5OS requires 380.154507.

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